Rich Jackim Wins Exit Planning Circle of Excellence Award

I was deeply honored to receive the 2025 Exit Planning Circle of Excellence Award from the Exit Planning Institute this week.

To the countless CEPAs I spoke with at the Exit Planning Summit, I am profoundly grateful for your heartfelt appreciation. Co-founding the Exit Planning Institute and creating the Certified Exit Planning Advisor (CEPA) training program and credential has been one of my life’s most rewarding achievements.

Your stories about how my book, “The $10 Trillion Opportunity,” transformed your careers and lives moved me beyond words.  Thank you!

It’s remarkable to witness EPI celebrating its 20th anniversary and flourishing with over 8,000 members worldwide.

Thank you to the Exit Planning Institute for this tremendous honor and for inviting me to participate in this year’s world-class Exit Planning Summit.

Rich Jackim, JD, MBA, CEPA

What’s Driving Acquisitions in the Jan-San Sector in 2025

Understanding the Active Janitorial Supply M&A Market in 2025

The janitorial supplies distribution and wholesale sector has seen remarkable M&A activity in recent years. For business owners in this space, understanding the dynamics of mergers and acquisitions has become increasingly important, whether you’re contemplating selling, exploring growth through acquisition, or simply positioning your company for long-term success.

Notable transactions involving private equity-backed firms like Imperial Dade and BradyIFS, as well as strategic buyers such as Veritiv, highlight the active nature of the market. For business owners approaching retirement, this heightened activity presents viable exit options so you can realize the value you’ve built over the years.

Key Drivers of Jan-San M&A Activity

Market Fragmentation and Consolidation Opportunities

The janitorial supplies industry remains highly fragmented, with the vast majority of companies operating with less than $10 million in revenue. This fragmentation creates significant opportunities for larger entities to pursue acquisitions as a means of rapidly expanding their footprint and gaining market share. Many small to mid-sized distributors find themselves competing in a market where scale increasingly matters, making strategic combinations an attractive path forward.

Strong Private Equity Interest

Private equity firms have demonstrated consistent interest in the janitorial sector, and it’s easy to understand why. These investors are attracted by the predictable revenue patterns that characterize the industry, along with the market fragmentation that creates natural roll-up opportunities. The strong margin profiles typical of well-run Jan-San distributors make them ideal candidates for platform investments, with subsequent add-on acquisitions to build scale and create operational synergies.

We’ve seen this strategy play out with PE-backed companies like Imperial Dade (an Advent portfolio company) and BradyIFS (initially backed by Kelso), both of which have been particularly active in acquiring smaller competitors to build national footprints.

Strategic Growth Initiatives

Beyond private equity, established distributors and wholesalers are actively pursuing M&A as a growth strategy. These strategic buyers are looking to expand their geographic reach into new territories, broaden their service offerings and product portfolios, and access new customer segments. Many find that acquisitions offer a faster and sometimes more cost-effective path to growth than organic expansion alone.

The integration of acquired businesses often yields cost efficiencies through combined purchasing power, streamlined logistics, and elimination of redundant overhead. For companies with strong integration capabilities, this can create significant value beyond the simple addition of revenue streams.

Technology and Efficiency Focus

The Jan-San industry is experiencing an increased emphasis on technology adoption and operational efficiency. Modern distribution businesses are embracing automation in janitorial equipment, developing IoT-enabled maintenance tools, and investing in sophisticated e-commerce capabilities. Those with integrated inventory management systems can deliver superior customer experiences while optimizing working capital.

Companies that have made these technological investments often become attractive acquisition targets for buyers looking to leapfrog their own digital transformation efforts. Rather than building these capabilities from scratch, many acquirers find it more efficient to purchase companies that have already successfully navigated the technology curve.

Succession or Exit Planning

One of the most persistent drivers of M&A activity is the aging demographic of business ownership. As founders and family business owners approach retirement, many find that selling provides the most viable succession solution. This approach allows them to realize the full value they’ve created, ensure business continuity for employees and customers, and preserve the legacy they’ve built over decades of work.

For many owners without family members interested in taking over the business, a strategic sale offers the best path to monetize their life’s work while ensuring the business continues to thrive under new ownership.

Stable Demand Post-Pandemic

The COVID-19 pandemic fundamentally changed attitudes about cleanliness and hygiene in commercial and public spaces. This heightened awareness has sustained demand for janitorial supplies well beyond the initial crisis period, making businesses in this sector particularly appealing to acquirers. Companies that demonstrated resilience and adaptability during the pandemic are especially attractive targets, as they’ve proven their ability to navigate significant market disruptions.

Valuing Your Janitorial Supply Company: Understanding Value Drivers

Understanding what drives value in janitorial supply businesses is crucial whether you’re preparing to sell or simply building long-term value. Buyers evaluate several key factors when determining what they’re willing to pay for a Jan-San distribution business.  For information on valuation multiples for Jan-San companies, please see our article How to Value a Janitorial Supply Company in 2025.

Revenue Quality and Stability

The stability and predictability of your revenue streams significantly impact valuation. Buyers place substantial value on businesses with consistent, recurring revenue backed by long-term customer contracts or relationships. Strong customer retention rates demonstrate the stickiness of your relationships and the quality of your service model.

A diversified customer base with limited concentration risk is particularly valuable, as it reduces the potential impact of losing any single client. Conversely, businesses with high customer concentration typically face more challenging valuations and often more complex deal structures designed to mitigate this risk for the buyer.

Financial Performance

When determining how to value a janitorial supply company, acquirers will thoroughly analyze your financial performance. EBITDA (earnings before interest, taxes, depreciation, and amortization) serves as the primary valuation metric, but buyers look beyond the raw numbers to understand the quality of those earnings.

They’ll examine profit margins and their stability or growth over time, cash flow generation patterns, and the sustainability of reported profits. Companies with stable or expanding margins typically command premium valuations as they demonstrate both operational efficiency and pricing power in the marketplace.

Management Team Strength

The depth and quality of your management team significantly impacts valuation, particularly for buyers who want to ensure business continuity post-acquisition. An experienced management team willing to stay after the transaction provides valuable continuity and institutional knowledge transfer.

Businesses that are overly dependent on the owner for key relationships and day-to-day operations may be viewed as higher risk acquisitions. In contrast, well-structured organizations with clear roles and responsibilities distributed across a capable team tend to command higher valuations and attract more buyer interest.

Operational Efficiency and Technology

Modern, efficient operations enhance business value by demonstrating scalability and future growth potential. Companies that have invested in e-commerce capabilities, integrated inventory management systems, and streamlined logistics networks are positioned to grow more efficiently.

Adoption of industry innovations and automation not only improves current profitability but signals to buyers that the business is forward-thinking and adaptable. These operational advantages often translate directly into higher valuations, as buyers recognize the embedded value of these investments.

Strategic Fit with Potential Buyers

The value of your business may vary significantly depending on the specific buyer. Strategic buyers might pay premiums for geographic expansion opportunities that complement their existing footprint. Private equity firms often value strong regional presence or defined market niches that can serve as platforms for further growth.

Complementary product lines can enhance your attractiveness to specific acquirers looking to round out their offerings. Understanding these strategic fit considerations helps position your business for optimal valuation with the right buyer pool.

Navigating the M&A Process: A Roadmap for Sellers

The M&A process involves several critical stages that janitorial supply business owners should understand to achieve optimal outcomes. While each transaction is unique, having a clear roadmap can help you navigate this complex journey more successfully.

Preparation: Positioning Your Business for Maximum Value

Before entering the market, thorough preparation is essential to maximize your company’s value and appeal. This preparation phase involves ensuring your financial statements are accurate and up-to-date, organizing customer and operational data, and populating a virtual data room with all the information a buyer will need during due diligence.

Understanding Your Business Value

A proper valuation of your business that will stand up to scrunty by a sophisticated buyer requires a comprehensive assessment that considers many factors unique to the Jan-San sector. Beyond the EBITDA multiples typical for distribution businesses, a thorough valuation will assess your company’s risk profile, examine customer retention history, analyze revenue concentration, and evaluate revenue and margin trends.

This valuation process not only provides you with a realistic price expectation but also identifies the value drivers within your business that can be emphasized during the marketing and negotiation phases. It also highlights areas that might need attention before taking the business to market.

Building Your Transaction Team

Successful transactions rarely happen without experienced advisors guiding the process. Your transaction team should include investment bankers with industry expertise who can identify and approach potential buyers while maintaining confidentiality. An M&A attorney familiar with your business can structure the transaction to protect your interests, while your CPA can provide essential accounting and tax guidance. The right advisory team not only maximizes transaction value but also significantly reduces the stress and uncertainty of the process.

Strategic Positioning and Marketing

Effectively presenting your business to potential buyers requires thoughtful preparation and positioning. This begins with developing compelling marketing materials that articulate your unique value proposition and growth potential. Identifying and proactively addressing potential buyer concerns helps maintain momentum throughout the process.

Your positioning strategy should emphasize the aspects of your business that will be most attractive to your likely buyer pool, whether that’s your customer relationships, operational efficiency, technological advantages, or geographic presence. This targeted approach helps buyers quickly recognize the strategic value your business offers.

Buyer Identification and Outreach

Identifying the right strategic and financial buyers requires working with an investment banker with experience in the Jan-San sector. Your investment banker will conduct targeted outreach to a targeted list of strategic and financial buyers that you approve to pitch a possible transaction and manage the flow of information to potential buyers, gradually providing more detailed information as buyers demonstrate serious interest and capability. This measured approach helps maintain competitive tension while protecting sensitive business information.

Deal Negotiation and Structuring

As interested buyers emerge, negotiations focuses not only on the purchase price but on the overall deal structure. Critical considerations include payment terms (cash at closing versus deferred payments), potential earn-out provisions, and the tax implications of different transaction structures.

The choice between an asset sale and a stock sale carries significant tax and liability implications that must be carefully evaluated. Your advisory team plays a crucial role in these negotiations, helping you understand the true economic value of different offers and structures.

Due Diligence Management

Once you’ve reached an agreement on basic terms, buyers will conduct comprehensive due diligence to verify their assumptions about your business. This process typically includes a detailed review of financial performance and projections, customer relationships and contracts, vendor agreements, employee matters, operational processes, and legal compliance.

Preparing for due diligence in advance helps the process proceed smoothly and minimizes the risk of issues arising that could impact the deal terms. A well-managed due diligence process maintains deal momentum while satisfying buyer requirements for verification.

Closing and Transition

The final stages of the transaction require attention to numerous details, from definitive agreement negotiation to working capital adjustments and transition service arrangements. Careful planning for employee communication and customer relationship transfers helps ensure business continuity throughout the ownership change.

A thoughtful transition plan addresses not only the legal and financial aspects of the deal but also the human and operational elements that will determine its ultimate success.

Beyond Price: Key Considerations When Selling

While maximizing value is important, successful Jan-San business owners consider multiple factors beyond the headline purchase price when evaluating potential transactions.

Financial Considerations

The structure of payment—upfront cash versus deferred consideration—can significantly impact the true value of an offer. Different deal structures carry varying tax implications that affect your after-tax proceeds. Potential ongoing financial ties to the business, such as seller financing or earn-outs, introduce risks that must be carefully evaluated against the potential upside they offer.

Your personal financial objectives and risk tolerance should guide these decisions, which is why it is so important to integrate your transaction planning with your overall wealth management strategy.

Operational Impact

The sale of your business will inevitably bring changes for your employees and operations. Understanding buyers’ integration plans and evaluating cultural compatibility helps ensure a smooth transition. Consider how potential changes to operations, branding, and customer relationships align with your vision for the business you’ve built.

Many sellers find that the treatment of long-time employees is a particularly important consideration in choosing the right buyer, even when it might come at the expense of maximizing sale price.

Risk Evaluation

Your business’s risk profile significantly influences both valuation and deal structure. Companies with high customer concentration typically receive lower multiples and more complex structures that shift some risk back to the seller through earn-outs or similar mechanisms.

Conversely, businesses with strong management teams independent of the owner and stable, growing revenue streams command premium valuations and more favorable terms. Understanding how buyers perceive your risk profile helps set realistic expectations and identifies opportunities to mitigate these risks before going to market.

Legacy Preservation

For many family-owned businesses, preserving the legacy they’ve built over decades is a primary concern. This often includes consideration of how the buyer will continue the business values and culture, treat long-term employees, and maintain the company’s reputation and community relationships.

While these factors may be difficult to quantify, they often prove decisive in selecting the right buyer from among multiple offers. Articulating these priorities early in the process helps your advisory team identify buyers whose vision aligns with yours.

Conclusion: Understanding Your Options Leads to Success

Whether your exit timeline is measured in months or years, understanding the M&A landscape allows you to make informed decisions. By focusing on the factors that drive value, building a strong advisory team, and carefully considering both financial and non-financial objectives, you can navigate the M&A process successfully.

As we’ve outlined above, the current environment presents significant opportunities for well-positioned janitorial supply distributors and wholesalers. If you work with an investment banker with Jan-San sector experience, like Jackim Woods & Co., you can achieve your business and personal goals while ensuring the continued success of the business you’ve built.

Jackim Woods & Co. provides investment banking and M&A advisory services to janitorial supply distributors and wholesalers throughout the United States. Our team of experienced professionals can help you navigate the complexities of selling your business or exploring acquisition opportunities in this dynamic market. Contact us to learn how we can help you achieve your strategic objectives.

About the Author and Jackim Woods & Co.

Rich Jackim is an janitorial supplies investment banker, entrepreneur, and former mergers and acquisitions attorney.

For the last 25 years, Rich has been providing boutique investment banking services to middle-market companies in a wide range of industries. He began focusing on the janitorial supply sector in 2020.

Rich also founded a successful training and certification company called the Exit Planning Institute, which he sold to a private equity group in 2012.

Rich is also the author of the critically acclaimed book, The $10 Trillion Dollar Opportunity: Designing Successful Exit Strategies for Middle Market Businesses.

Jackim Woods & Co offers skilled mergers and acquisitions advisory services to privately owned janitorial supply and building services companies in both sell-side and buy-side transactions. Jackim Woods & Co has arranged over 100 successful transactions, ranging from less than one million to more than eighty million dollars in value.

If you own a janitorial supply or building services business and would like to explore your options, I would welcome an opportunity to speak with you.

Feel free to contact me at 224-513-5142 or rjackim@jackimwoods.com.

Jackim Delivers Presentation on Business Valuation at SSIA Conference

Rich Jackim, JD, MBA, of Jackim Woods & Company and Sports Club Advisors, delivered an insightful presentation entitled “Mergers & Acquisitions in the Sports & Social Industry” at the 2025 Sport & Social Industry Association (SSIA) Conference in Las Vegas. Jackim has been involved in 9 transactions in the sports and social industry, on either the buy-side or sell-side.

The session drew a packed house of sports and social league owners and operators who were eager to learn about key aspects of business valuation in their sector.

Mr. Jackim’s presentation covered crucial topics designed to enhance the attendees’ understanding of mergers and acquisitions, including:

• How to value a sports & social league
• Identifying the key factors buyers look at when evaluating a league
• Understanding who the most likely buyers are for your business
• How these concepts can be used to increase the value of a business

Drawing on his expertise in mergers & acquisitions, valuations, and strategic planning in the sports and social industry, Mr. Jackim shared his thoughts on the current M&A market for sports and social leagues and a basic valuation formula that is more accurate and useful than the rules of thumb that are commonly used. He emphasized that while rules of thumb might seem easy, they are “almost always wrong” because they don’t consider the specific nuances of each business.

Attendees also gained valuable knowledge from “Done Deals and Lessons Learned” case studies, including acquisitions made by FXA Sports and Austin Sports & Social Club (ASSC).

The presentation ended with Jackim providing actionable advice on “Ways to Build Value in Your Club,” such as having the right legal and ownership structure and diversifying revenue streams.

For a copy of this presentation, please contact us at rjackim@jackimwods.com.

About the Presenter and Jackim Woods & Co.

Rich Jackim is an business broker, education industry entrepreneur, and former mergers and acquisitions attorney.

For the last 25 years, Rich has been providing boutique investment banking services to middle-market companies.

Rich also founded a successful training and certification company called the Exit Planning Institute, which he sold to a private equity group in 2012.

Rich is also the author of the critically acclaimed book, The $10 Trillion Dollar Opportunity: Designing Successful Exit Strategies for Middle Market Businesses.

Jackim Woods & Co offers skilled mergers and acquisitions advisory services to privately businesses, including nine sports and social leagues, in both sell-side and buy-side transactions. Jackim Woods & Co has arranged over 100 successful transactions, ranging from less than one million to more than eighty million dollars in value.

If you own a sports and social league and are interested in exploring your options, I would welcome an opportunity to speak with you. Feel free to contact me at 224-513-5142 or rjackim@jackimwoods.com.

How to Value a Trucking Business in 2025

If you’re considering selling your trucking business, determining its value is the first step. This guide will walk you through the key aspects of valuing a trucking company in 2025, combining expert insights and current market trends to help you understand what your business is worth.

Why is Valuation Important?

Understanding your company’s value is essential for several reasons:

• Setting a realistic sale price: A proper valuation helps you set a realistic asking price, attracting serious buyers and avoiding wasted time.  The number one reason companies don’t sell is that sellers have unrealistic expectations of value. So getting this right from the start is essential.
• Negotiating effectively: Knowing your company’s value empowers you to negotiate favorable terms.
• Making informed decisions: Valuation provides a clear picture of your company’s financial health and potential, guiding your decisions throughout the sale process.

Factors That Affect the Sale Price

The ultimate sale price of your trucking company depends on a variety of factors:

• Business location: A business operating in a busy hub or serving a busy city will command a higher price.
• Asset value: Tangible assets (trucks, trailers, equipment) and intangible assets (goodwill, brand recognition) increase the sale price, especially when they generate significant revenue.
• Condition of the trucking fleet: Well-maintained trucks with good fuel efficiency are highly desirable.
• Prevailing market conditions: The overall health of the market affects valuation. A market slump can lower the sale price.
• Historical earnings and finance trends: Consistent earnings, positive financial trends, cost control, and a strong credit history are all significant pluses.
• Reliance on the owner: Buyers assess whether the business can sustain profits after the owner’s exit.
• Growth potential: A business with clear growth potential, such as an expanding customer base, is more valuable.
• Legal history: A clean legal history is essential.
• Client base: A large and reliable client base increases the sale price.
• Brand recognition and reputation: A reputable brand is a valuable asset.

Trucking Company Valuation Methods 

Here are several methods you can use to determine the value of your trucking company:

• Market Approach: This involves analyzing past market transactions of similar trucking companies to establish a valuation basis. However, accessing transaction data for privately owned trucking companies can be challenging. Public companies offer more transparency due to publicized M&A activity.
• Cost-based Valuation: This approach calculates the cost of creating a similar company from the ground up, including tangible and intangible assets.
• Asset Approach: This method determines the net value of a business’s assets minus its liabilities. It’s crucial to use the market value of your equipment and factor in goodwill or intangible value.
• EBITDA Multiples: This common approach applies an industry multiple to your company’s EBITDA (Earnings Before Interest, Taxes, Depreciation, and Amortization).

Understanding EBITDA Multiples for Trucking Companies

EBITDA is a key metric for valuing trucking companies. Here’s how to calculate it:

EBITDA = Net income + Interest + Taxes + Depreciation + Amortization

EBITDA for Privately Owned Trucking companies is slightly different.

Adjusted EBITDA = Net income + Interest + Taxes + Depreciation + Amortization + Owner Addbacks – CAPEX (capital expenditures)

To determine your company’s value using EBITDA, you’ll need to calculate the company’s Enterprise Value:

Enterprise Value = Adjusted EBITDA x EBITDA Multiple

Finally, estimate your company’s value:

Your trucking company’s value = Adjusted EBITDA x EBITDA Multiple (see below)

Your trucking company’s value = Adjusted EBITDA x EBITDA Multiple (see below)

Current EBITDA Multiples for Trucking Companies in 2025

Despite a very difficult freight market for the last several years, the average EBITDA multiples for privately owned trucking companies still ranges between 5x and 8x. However, these multiples can vary significantly based on company type and revenue range:

EBITDA Multiples for Privately Owned Trucking Companies, Q1 2025

It is important to note that these multiples are current as of Q4 2024 and are subject to change.

Revenue Multiples for Privately Owned Trucking Companies, Q1 2025

It is important to note that these multiples are current as of Q4 2024 and are subject to change.

Other Factors Affecting the Value of a Trucking Company

The type of trucking company also impacts valuation:

• Asset-based: Companies that own their fleets and facilities are typically less valuable that companies that lease everything. Asset-light companies receive slightly higher valuations due to lower costs and risks. Buyers show a preference for asset-light operations because of their ability to quickly adapt to changing market conditions.
• LT vs LTL: Companies that focus on long-haul freight are more valuable that less-than-truckload carriers.
• Specialized Equipment: Companies that run a lot of specialized equipment like reefers, tankers, or oversized flatbeds are more valuable than dry van carriers.
• Long-haul vs Short-haul:  Long-haul carriers are valued higher that short haul carriers.

Steps to Prepare Your Trucking Company for Sale

Once you understand the factors influencing value, take these steps to prepare for a sale:

1. Get in the Right Mindset: Be certain about your decision to sell and clear on your reasons. Determine the best time to sell, like when revenues are high or before a significant market shift. Plan what you’ll do after the sale.
2. Prepare Detailed Financial Documents: Organize financial records to demonstrate your business’s profitability. Key documents include:
   • Income statements
   • Balance sheets
   • Tax returns for the last 3 years
   • List of equipment (trucks, trailers, etc.)
   • Current agreements and contracts
   • Make sure your adjusted EBITDA calculation is correct
   • Cash flow statements
   • Credit statements
   • List of clients
   • Have your M&A advisor create a virtual data room to organize and store this information so its easily available to potential buyers
3. Address Legal Considerations: Ensure your business is legally sound by having the following easily available for a buyer to review:
   • Taxes and tax returns
   • Company bylaws
   • Partnership agreements
   • Privacy agreements
   • Meeting minutes
   • Details of any ongoing legal proceedings
   • Contracts with clients, employees, and suppliers
   • Intellectual property records (trademarks, etc.)
   • Existing leases
   • Have your M&A advisor create a virtual data room to organize and store this information so its easily available to potential buyers
4. Increase Value and Sellability: Improve your business to attract buyers. Diversify income sources and consider these enhancements:
   • Invest in well-maintained equipment, if necessary
   • Expand your customer base if possible
   • Enhance customer relationships and vendor partnerships
   • Embrace new technology
   • Implement systems for smooth operation without the owner’s daily involvement
   • Reduce debt if possible
   • Develop a strong management team
   • Reduce operational costs
   • Set up systems for a smooth transition
   • Resolve any outstanding legal issues
5. Hire an M&A Expert: An experienced M&A team can help you market your business, vet potential buyers, and finalize the sale agreement. They can include wealth advisors, investment bankers, accountants, and attorneys.
6. Market Your Company: Your M&A team will market your business to potential buyers. Your M&A advisor may also use online platforms, social media, and networking events.
7. Negotiate Favorable Sales Terms: Work with your M&A team to negotiate an attractive sale price and deal structure
8. Participate in Due Diligence: Cooperate with the buyer’s due diligence process by providing necessary records and answering questions
9. Finalize the Sale and Transfer: Complete the sale and transfer assets
10. Ensure a Smooth Transition: Help the new owner settle into the business by providing support and training

Trends in Trucking M&A in 2025

Several trends are shaping the M&A landscape for trucking companies in 2025:

• Preference for Asset-Light Operations: Buyers are increasingly favoring asset-light companies due to their lower operational costs
• Higher Value for Specialized Trucking Companies: Niche trucking operations with strong client relationships are attracting more interest
• Increased Deal Volume: With improving financing conditions, deal volume is expected to rise as acquirers consolidate smaller companies

The Value of Expert Guidance

Selling a trucking company is a time intensive and complex undertaking. Engaging experienced M&A advisors can significantly increase your chances of a successful sale at the best possible price. An M&A advisor with experience in the trucking and transportation sector can:

• Help you accurately value your business
• Prepare necessary offering documents and financial models
• Market your company effectively to financial and strategic buyers
• Negotiate favorable terms
• Manage the due diligence process
• Ensure a smooth closing and transition

By understanding the key valuation methods, market trends, and preparation steps, you can confidently navigate the sale process and achieve the best possible outcome for your trucking business.

About the Author and Jackim Woods & Co.

Rich Jackim is an trucking industry investment banker, entrepreneur, and former mergers and acquisitions attorney.

For the last 25 years, Rich has been providing boutique investment banking services to middle-market companies in a wide range of industries. He began focusing on the trucking and transportation sector in 2003 and wrote the Guide to Value Your Trucking Company, published by the American Trucking Association from 1997-2002.

Rich also founded a successful training and certification company called the Exit Planning Institute, which he sold to a private equity group in 2012.

Rich is also the author of the critically acclaimed book, The $10 Trillion Dollar Opportunity: Designing Successful Exit Strategies for Middle Market Businesses.

Jackim Woods & Co offers skilled mergers and acquisitions advisory services to privately owned trucking and transportation companies in both sell-side and buy-side transactions. Jackim Woods & Co has arranged over 100 successful transactions, ranging from less than one million to more than eighty million dollars in value.

If you own a trucking or transportation company and are interested in exploring your options, I would welcome an opportunity to speak with you.

Feel free to contact me at 224-513-5142 or rjackim@jackimwoods.com.

Acquisitions in the Legal Tech Sector in 2025

Acquisitions in the Legal Tech Sector in 2025

The following is a summary of mergers and acquisitions transactions expected in the legal tech sector in 2025. This article will be updated every two weeks as we work with more clients and learn of other deals in the sector.

The legal tech sector experienced a burst of interest in 2024 as artificial intelligence became a focal point for many tech-enabled businesses, and people quickly understood its applications in the legal field.

As a result, valuations for small, medium, and large legal tech companies have gone up significantly in the last 18 months and are higher than valuations for traditional businesses. The average small to medium-sized legal tech company is valued at 2x to 3x trailing twelve-month annual recurring revenue or 7x to 9x trailing twelve-month EBITDA.

Reported Acquisitions in the Legal Tech Sector in 2025

Below is a summary of the mergers and acquisition transactions in the legal tech in 2025. This is not an exhaustive list, as many smaller transactions are never announced. This list represents the deals we have learned about through our network or that we are directly involved in, and will be updated every two weeks.

In February

• Baretz+Brunelle, a consulting firm focused on driving growth in the legal industry, acquired LexFusion, a legal services provider that helps accelerate legal tech adoption.
• Factor, a tech-driven alternative legal services provider, acquired Theory and Principle, a legal-focused design and development agency.
• LegalZoom, a legal and business services provider, acquired Formation Nation, a small business formation and compliance provider.
• Litera, a comprehensive tech-enabled productivity platform for law firms, acquired Peppermint Technology, a matter management and CRM platform for law firms.
• StructureFlow, a developer of tools to visualize complex legal structures, acquired Blue J Diagramming, a tax visualization and diagramming tool used by law firms.
• Veritext, a technology-driven court reporting and litigation support provider, acquired Resolute Systems, an alternative dispute resolution service provider, and The McCammon Group, another alternative dispute resolution service provider.
• Thirdfort, a developer of digital onboarding and payments systems for real estate, acquired Homeppl, a fraud prevention tool.

Veritext, a technology-driven court reporting and litigation support provider, acquired Upchurch Watson White & Max, alternative dispute resolution service provider.

In January

• Elevate, a provider of legal software and law firm support services, acquired Sagacious IP, a patent and intellectual property research company.
• Elite, a law firm business operations platform, acquired Tranch, a leading B2B invoice automation and payments platform offering invoice management and payment options for law firms and their clients.
• Onit, a no-code AI platform that automates enterprise legal workflows, acquired Legal Files, a legal case management software.
• SurePoint Technologies, a developer of cloud-based software for law firms’ financial management, acquired ZenCase, a legal software that automates law firm operations and tracking.
• The L Suite, a peer network of in-house legal executives, acquired Luminate+, an e-learning platform for in-house lawyers.
• ZwillGen, a law firm with various specialty technology practices, acquired Luminos.Law, a multidisciplinary firm that blends legal advisory services with data analytics, to help clients better understand and effectively deploy transformative artificial intelligence technology

Factors Driving Deal Activity

• Continued Consolidation: Expect to see continued consolidation in various segments of the legal tech market. This will be driven by companies seeking to expand their management teams, grow their product offerings, enter new markets, achieve economies of scale, and integrate emerging technology.
• Private Equity Activity: Private equity firms will remain active in the legal tech space. These firms will be looking for companies with strong growth potential and recurring revenue models. We can also expect to see larger deals involving established players in the market, as well as smaller acquisitions of emerging startups.
• Focus on AI and Emerging Technologies: While AI presents an existential risk for some traditional legal services businesses, law firms that that leverage artificial intelligence and other emerging technologies to improve client outcomes and lower costs will thrive.

About the Author and Jackim Woods & Co.

Rich Jackim is an legal tech industry investment banker, edtech entrepreneur, and former mergers and acquisitions attorney.

For the last 25 years, Rich has been providing boutique investment banking services to middle-market companies in a wide range of industries.

Rich also founded a successful training and certification company called the Exit Planning Institute, which he sold to a private equity group in 2012.

Rich is also the author of the critically acclaimed book, The $10 Trillion Dollar Opportunity: Designing Successful Exit Strategies for Middle Market Businesses.

Jackim Woods & Co offers skilled mergers and acquisitions advisory services to privately owned legal tech, court reporting, and litigation support companies in both sell-side and buy-side transactions. Jackim Woods & Co has arranged over 100 successful transactions, ranging from less than one million to more than eighty million dollars in value.

If you own an legal tech, court reporting, and litigation support business and are interested in exploring your options, I would welcome an opportunity to speak with you.

Feel free to contact me at 224-513-5142 or rjackim@jackimwoods.com.

How to Value a Legal Tech Company: Key Factors for Buyers and Sellers in 2025

As the legal technology sector continues to evolve and mature, understanding the key value drivers for Legal Tech companies has become increasingly important for both buyers and sellers. At Jackim Woods & Co., our unique perspective combines deep investment banking expertise with firsthand legal industry knowledge. Our founder, Rich Jackim, a former White & Case attorney, uses his investment banking and legal experience to provide nuanced insights into legal tech valuations.

Critical Valuation Drivers in Legal Tech

Revenue and Profitability Metrics

Financial performance remains the cornerstone of any valuation analysis. In the legal tech sector, companies employ various revenue models that require careful evaluation. Subscription-based models often provide predictable, recurring revenue streams that investors value highly. Usage-based pricing can offer greater upside potential but may introduce more variability. Tiered pricing structures can effectively capture value across different customer segments while providing opportunities for upselling.

Our analysis extends beyond top-line numbers to examine profitability margins and operational efficiency. We evaluate how effectively companies convert revenue into profit, considering factors such as customer acquisition costs, development expenses, and overhead. The sustainability of current financial performance is particularly critical in the legal tech sector, where rapid technological change can quickly impact business models.

Market Position and Competitive Dynamics

The legal tech landscape is experiencing significant consolidation, with market share increasingly concentrated among key players. This consolidation creates both opportunities and challenges for companies in the space. Strong market positions become more valuable as barriers to entry rise, while smaller players must demonstrate clear differentiation or growth potential to maintain competitive positions.

Our team conducts detailed analyses of competitive positioning, examining how companies create and maintain advantages in their chosen market segments. Strategic partnerships often play a crucial role, particularly those that enable integration with established legal workflow systems. We evaluate how effectively companies leverage these relationships to expand their market reach and enhance their value proposition.

Intellectual Property Assets

Having served the legal industry for decades, we understand that intellectual property protection is fundamental to maintaining competitive advantages in legal tech. A robust IP portfolio serves multiple purposes in driving valuation. Patents can protect core technologies and create barriers to entry, while trademarks safeguard brand value and market position. Proprietary technology, particularly when it addresses specific pain points in legal workflows, can command premium valuations.

The potential for IP monetization through licensing adds another dimension to valuation analysis. Rich Jackim’s legal background proves particularly valuable in assessing the strength and enforceability of IP portfolios, as well as their potential for generating additional revenue streams.

Customer Base Analysis

The composition and stability of a company’s customer base significantly impacts valuation. We examine customer concentration to assess risk, looking for healthy diversification across firm sizes and practice areas. Retention rates provide crucial insights into product stickiness and customer satisfaction, while contract terms and renewal patterns help predict future revenue stability.

Understanding customer acquisition costs relative to lifetime value reveals the efficiency of a company’s growth strategy. In the legal tech sector, where adoption can be gradual and relationship-driven, these metrics help predict scalability and long-term profitability.

Technology Infrastructure and Scalability

In today’s rapidly evolving legal tech landscape, scalable technology infrastructure is crucial for maintaining competitive advantages and supporting growth. We evaluate platform flexibility and adaptability, considering how easily systems can accommodate new features, increased user loads, and emerging technologies. Integration capabilities with existing legal systems often prove critical for adoption and retention.

Development roadmaps and innovation potential factor heavily into our analysis, as does the assessment of technical debt and maintenance requirements. Companies with modern, well-maintained technology stacks typically command premium valuations due to their reduced risk profile and greater growth potential.

Regulatory Compliance Framework

Drawing on Rich Jackim’s legal background, we place particular emphasis on evaluating a company’s regulatory compliance infrastructure. In the legal tech sector, robust data privacy and security measures are non-negotiable. We assess how companies protect sensitive client information and maintain compliance with evolving privacy regulations.

Professional conduct compliance takes on special importance in legal tech, where software often interfaces with regulated legal processes. Risk management frameworks and the ability to adapt to regulatory changes can significantly impact valuation, as buyers increasingly scrutinize compliance capabilities during due diligence.

Economic and Market Conditions

Broader market dynamics significantly influence valuation multiples in legal tech. Industry growth rates and technological advancement cycles can affect how the market values different business models and capabilities. Economic conditions affecting legal services often directly impact demand for legal tech solutions, making it essential to consider these factors in valuation analyses.

Valuation Multiples in the Legal Tech Sector

Factors Influencing Legal Tech Company Multiples

The Current M&A Landscape in Legal Tech

The Jackim Woods & Co Advantage

Our unique combination of legal industry experience and investment banking expertise allows us to provide comprehensive valuation services tailored to the legal tech sector. Rich Jackim’s background as an attorney with White & Case and investment banker with Prudential Capital provides invaluable insights into the specific needs and challenges of legal technology companies. This dual perspective enables us to identify value drivers that might be overlooked by firms lacking deep industry knowledge.

About the Author and Jackim Woods & Co.

Rich Jackim is an legaltech industry investment banker, edtech entrepreneur, and former mergers and acquisitions attorney.

For the last 25 years, Rich has been providing boutique investment banking services to middle-market companies in a wide range of industries.

Rich also founded a successful training and certification company called the Exit Planning Institute, which he sold to a private equity group in 2012.

Rich is also the author of the critically acclaimed book, The $10 Trillion Dollar Opportunity: Designing Successful Exit Strategies for Middle Market Businesses.

Jackim Woods & Co offers skilled mergers and acquisitions advisory services to privately owned legal tech, court reporting, and litigation support companies in both sell-side and buy-side transactions. Jackim Woods & Co has arranged over 100 successful transactions, ranging from less than one million to more than eighty million dollars in value.

If you own an legal tech, court reporting, and litigation support business and are interested in exploring your options, I would welcome an opportunity to speak with you.

Feel free to contact me at 224-513-5142 or rjackim@jackimwoods.com.

Acquisitions in the Education & EdTech Sector in 2025

Acquisitions in the Education and Edtech Sectors in 2025

The following is a summary of mergers and acquisitions transactions expected in the education and edtech sectors in 2025. This article will be updated every two weeks as we work with more clients and learn of other deals in the sector.

The education and edtech sectors experienced a slow start in 2024. Many smaller deals in 2024 fell apart during due diligence. Rising interest rates created anxiety around borrowing costs caused buyers to require a higher return on their investment and depressed valuations.

Investors were still recovering from the bad decisions they made during the COVID pandemic. Most EdTech investors have adopted a more cautious approach after making investments at inflated valuations during the COVID era. Post-COVID, many segments of the education sector have been shaken up due to increased regulation of for-profit Title IV vocational colleges and concerns about the expiration of ESSER funds.

As a result, valuations for small, medium, and large edtech companies have returned to pre-COVID levels, although they are still higher than valuations for traditional businesses. The average small and medium-sized edtech company is valued at 2x to 3x trailing twelve-month annual recurring revenue.

Reported Acquisitions in the Education and Edtech Sectors in 2025

Below is a summary of the mergers and acquisition transactions in the education and edtech sectors in 2025. This is not an exhaustive list, as many smaller transactions are never announced. This list represents the deals we have learned about through our network or that we are directly involved in, and will be updated every two weeks.

In March,

• Pryor Learning, LLC  acquired PeopleKeys, Inc.  to expand Pryor’s capabilities to offer market-leading DISC assessments and benchmarking analytics as part of its training and learning curriculum.
• Niche, a Canadian K-12 and college discovery platform, has acquired Goodkind, a startup that helps colleges and schools connect with prospective students.

In February,

• Commercial Services Group, a UK-based logistics firm, acquired WF Education Group to build marketshare across the UK and France.
• The Riverside Company, a US investment firm, acquired Wall Street Prep (WSP), a financial training provider, to expand its market share in financial training services.
• Sparkrock, a US-based enterprise software provider, acquired School-Day, a leading payment and activity management platform for schools.
• Elsmere Education, which helps higher education institutions manage online programs, merged with HCRC to offer enrollment and retention solutions.
• Dallas-based Barbri Global, which sells bar exam preparation courses acquires legal learning company Quimbee, a platform that provides study guides for law students
• BetterLesson, a K-12 professional learning provider, acquired Always Be Learning (Abl), to enhance its support for school districts with student scheduling and programming.

In January

• Cengage Group, a US-based curriculum resource provider, acquired Visible Body, a provider of interactive 3D models and software for science education.
• Wayable, a Canadian platform specialized in support for international students, acquired Psymood, a mental health and mentorship provider targeted at international students.
• Brightchamps, a Singaporean curriculum resource provider, acquired Edjust, a provider of digital solutions for personalized education. With this acquisition, GSV Ventures-backed Brightchamps has acquired four companies, including Education10x, a financial literacy education platform for children, Schola, a live learning platform for kids, and Metamorphosis Edu, which trains students in skills linked to entrepreneurship.

Factors Driving Deal Activity

• Continued Consolidation: Expect to see continued consolidation in various segments of the edtech market. This will be driven by companies seeking to expand their product offerings, enter new markets, and achieve economies of scale. For example, companies with complementary product offerings might merge to offer more comprehensive solutions.
• Private Equity Activity: Private equity firms will remain active in the education and edtech space. These firms will be looking for companies with strong growth potential and recurring revenue models. We can also expect to see larger deals involving established players in the market, as well as smaller acquisitions of emerging startups.
• Focus on AI and Emerging Technologies: While AI presents an existential risk for some traditional online education companies, businesses that leverage artificial intelligence and other emerging technologies to improve learning outcomes will be attractive targets. This includes AI-powered tutoring platforms, adaptive learning systems, and platforms that personalize learning content.
• Continued Emphasis on K-12 and Higher Education: Deals involving K-12 learning solutions, higher education platforms, and workforce development solutions will remain prominent.
• Companies focused on the Skills Gap: Companies that provide upskilling and reskilling are becoming central to education pathways. Work-integrated learning models—internships, apprenticeships, and co-op programs—are gaining traction in the United States, aligning student education with industry needs. Vocational training has emerged as a pragmatic choice for many learners. Collaborations between traditional academic institutions and industries are creating seamless pathways from education to employment, addressing local talent shortages. Governments are incentivizing practical training, making it faster and less expensive for students to enter in-demand jobs.

Additional Factors to Consider

• Valuation Pressure: The valuation of edtech companies may continue to face pressure due to the recent market corrections and ongoing economic uncertainties. Buyers are likely to remain cautious and selective, emphasizing profitability and sustainable growth.
• Impact of ESSER Funds: The expiration of ESSER funds will likely continue to influence K-12 spending, which may impact the strategies of EdTech companies in that space.
• Impact of Byju Bankruptcy: The 2024 bankruptcy of Byju and Prosus writing off it’s investment will likely depress valuations in the edtech sector and create a flood of deals on the market.
• Impact of AI on Education.  While AI presents some exciting opportunities for education, it presents an existential threat for others.  See our article on the impact of AI on the Coding Bootcamp Sector.

About the Author and Jackim Woods & Co.

Rich Jackim is an education industry investment banker, education industry entrepreneur, and former mergers and acquisitions attorney.

For the last 25 years, Rich has been providing boutique investment banking services to middle-market companies in the education sector.

Rich also founded a successful training and certification company called the Exit Planning Institute, which he sold to a private equity group in 2012.

Rich is also the author of the critically acclaimed book, The $10 Trillion Dollar Opportunity: Designing Successful Exit Strategies for Middle Market Businesses.

Jackim Woods & Co offers skilled mergers and acquisitions advisory services to privately owned schools, colleges, and EdTech companies in both sell-side and buy-side transactions. Jackim Woods & Co has arranged over 100 successful transactions, ranging from less than one million to more than eighty million dollars in value.

If you own an education-related business and are interested in exploring your options, I would welcome an opportunity to speak with you. Feel free to contact me at 224-513-5142 or rjackim@jackimwoods.com.

Mid 2023 Recreational Vehicle Industry M&A Report

This article is a summary of recent M&A activity in the recreational vehicle industry in 2023.

The recreational vehicle industry is coming off two of the most profitable and demanding years in a row. The effects of the COVID-19 pandemic and economic shutdown greatly benefited all aspects of the industry, from manufacturers, dealers, repairs, and campgrounds. The companies that were ready capitalized greatly and added a new generation of customers to its base. But now what? 2023 is proving to be a very different year for all involved.

Recent Mergers and Acquisitions

Despite the recent slowdown in the RV industry as a whole, mergers, and acquisitions are still going strong. Marcus Lemonis, Chairman and CEO of Camping World, recently said, “Our goal is to achieve 50% growth in our store count over the next five years”. Camping World is currently the largest retailer of RVs and has 197 store locations. Many other conglomerates are looking to expand via acquisitions and new store openings.

By Craig Hudman, Managing Director at Jackim Woods & Co.

Jackim Woods & Co. is a leading mergers and acquisition advisor focused on providing senior-level attention and flawless execution to clients in the recreational vehicle industry.

Craig is an experienced mergers & acquisitions professional, a former owner of a leading RV dealer, and a dealership management and operations expert. He brings over 30 years of RV-related experience.

To arrange a free, confidential initial consultation, please contact Craig Hudman at (208)521-1521 or chudman@jackimwoods.com.

Kahoot Goes Private for $1.7 Billion in All Cash Deal

The popular education game developer Kahoot has gone private in a $1.7 billion all-cash deal.

At that valuation, the buyers of Kahoot, an Oslo-based developer that built and runs the popular quiz tool, paid a significant premium. But it’s still below the company’s COVID-era valuation, which valued the company at closer to $6 billion.

The Kahoot buyer group was led by Goldman Sachs’ private equity arm, with General Atlantic, KIRKBI Invest A/S (of LEGO Group), and Glitrafjord named as major investors.

Kahoot was listed on the Oslo Stock Exchange and went public in 2021. That same year, Kahoot acquired Clever, a platform developer that streamlined the edtech experience for schools, and according to their websites,  says it serves half of all K-12 students in the U.S.

The premium price paid for Kahoot is an exception to the rule these days, as edtech companies find themselves in a more conversation valuation climate than the valuations paid during the pandemic. The visions many investors had of unlimited edtech growth, which fueled crazy valuations like Byju’s, have fallen apart, says Rich Jackim of Jackim Woods & Company, and valuations have returned to the more normal valuations seen for other SaaS companies.

In Jackim’s estimation, the new owners are likely to draw Kahoot and Clever farther from their roots, which raises questions about what the future direction of the company will be and whether Kahoot will continue to offer the Clever platform to schools for free for much longer.

If you own an education, training or edtech company and would like to explore your options, please contact Rich Jackim at rjackim@jackimwoods.com or 224-513-5142.

Mid 2023 Recreational Vehicle Industry Report

The recreational vehicle industry is coming off two of the most profitable and demanding years in a row. The effects of the COVID-19 pandemic and economic shutdown greatly benefited all aspects of the industry, from manufacturers, dealers, repairs, and campgrounds. The companies that were ready capitalized greatly and added a new generation of customers to their base. But now what? 2023 is proving to be a very different year for all involved.

The RV Industry as a whole is seeing the effects of record sales in the past two years. Sales have plummeted in part to the rising costs of RV and interest rate hikes. RV shipments in 2023 are at their lowest point since 2007-2008. Many dealers are still struggling to move new 2022 model year units while manufacturers slowly roll out 2024 model years. Projections put shipments in 2023 around 300,000 and 2024 in the mid 300’s. This added on top of interest rates that have nearly doubled over the last twelve months, and a poor national economic outlook has put most would-be buyers on hold. Interest rates are not expected to decrease until the latter part of 2024.

The RV Industry as a whole had an overall economic impact of $140 billion in 2022. More Americans are discovering the joys of camping. The average use of an RV is around 20 days per year. Manufacturers, Dealers and Campgrounds are staying busy with the huge influx of new buyers coming to the RV market as a result of the COVID-19 pandemic. These new customers are keeping both campgrounds and dealerships busy, not to mention the added strain on manufacturers and suppliers.

Thor, Forest River, and Winnebago account for 90% of all RV’s manufactured in the U.S. and Canada. These three “big” manufacturers continue to dominate and account for all brands commonly sold on most dealers’ lots. Towables account for close to 90% of the market, and the other 10% is motorized. Thor leads the way in towables and motorized market share, and Forest River is number two. The largest segment growth comes in the motorized class B with growth of around 8% per year. Winnebago currently claims 39% of this market. Texas continues to be the number one destination for wholesale RV shipments at nearly 10%, followed by California (6.4%), Florida (6.1%), Ohio (3.6%), and Michigan (3.5%). The median age for RV buyers has dropped to 33 years old. The amount financed on an RV has risen to around $45,000.

By Craig Hudman, Managing Director at Jackim Woods & Co., a leading mergers and acquisition advisor focused on providing senior-level attention and flawless execution to clients in the recreational vehicle industry.

Craig is an experienced mergers & acquisitions professional, a former owner of a leading RV dealer, and a dealership management and operations expert. He brings over 30 years of RV-related experience.

To arrange a free, confidential initial consultation, please contact Craig Hudman at (208)521-1521 or chudman@jackimwoods.com.