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Middle Market Mergers and Acquisitions by Colonnade Advisors

Middle Market Mergers and Acquisitions by Colonnade Advisors

By: Gina Cocking and Jeff Guylay
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 Get the insiders’ take on mergers and acquisitions. M&A investment bankers Gina Cocking and Jeff Guylay of Colonnade Advisors discuss the technical aspects of and tactics used in middle market deals. This podcast offers actionable advice and strategies for selling your company and is aimed at owners of middle market companies in the financial services and business services sectors. Middle market companies are generally valued between $20 million and $500 million.All rights reserved Economics Management Management & Leadership
Episodes
  • MM M&A - 030: Why Hire an Advisor

    MM M&A - 030: Why Hire an Advisor
    Apr 15 2025
    In this episode, host Jeff Guylay is joined by guest Mark Achler, co-author of Exit Right, to explore the critical decision of whether—and when—to hire advisors during the M&A process. Drawing on lessons from the book and real-world experience, Jeff and Mark outline how CEOs can maximize value by assembling the right team of experts, while still retaining control over strategy, relationships, and execution. From bankers and attorneys to financial planners and tax professionals, this episode offers actionable insights on selecting advisors who align with your values and contribute meaningfully to successful outcomes. What You’ll Learn in This Episode: The spectrum of advisors involved in a typical M&A transaction Why hiring early—especially pre-LOI—creates leverage and unlocks value How to avoid becoming overly dependent on advisors The CEO’s role in maintaining judgment, relationships, and deal momentum Why trust between parties is the foundation of successful dealmaking How detailed LOIs and clear integration planning drive better outcomes Real-world case studies showing how applying these principles boosted valuations Key Discussion Points & Notable Quotes: The Spectrum of Advisors in a Deal (00:43) Mark and Jeff review the key players involved in M&A: attorneys, bankers, tax advisors, financial planners. Timing matters—especially when it comes to financial planning and structuring decisions. “You want the best experts early—not just after the deal is done.” – Mark The CEO’s Non-Negotiable Responsibilities (03:48) Even with great advisors, CEOs must lead on strategy, decisions, and relationships. “There are some things you just can’t outsource. You can’t outsource judgment or trust.” – Mark The Importance of Trust in Getting Deals Done (05:46) Advisors can facilitate—but it’s the trust between principals that often moves a deal forward. “Trust is the lubrication that gets deals across the finish line.” – Mark The Role of the Banker and the Importance of Timing (06:17) A good banker understands the full arc of a transaction and helps prioritize forward-looking rationale over backward-looking valuation. “We’re not just selling the past EBITDA—we’re building the case for future synergy.” – Jeff When to Step in as a CEO (08:13) The back-and-forth between attorneys can derail progress. CEOs must often step in to resolve what really matters. “There’s always a point in a deal when someone has to say, ‘Enough—we need to solve this as principals.’” – Jeff Detailed LOIs Preserve the Deal’s Integrity (10:41) Without a clearly written LOI, sellers lose leverage and risk misinterpretation later. “The minute you sign the LOI, you lose 90% of your negotiating leverage.” – Mark “Our role as advisors is to make sure the LOI is translated accurately into legal documents.” – Jeff The Case for the Right Advisor (13:18) Not all advisors add value—some derail deals. Founders must choose those aligned with their values and goals. “This is your baby. Choose someone who gets it, who gets you.” – Mark “You’re essentially choosing a best friend for a very intense experience.” – Jeff Real-World Success: A Valuation Doubled (18:54) Mark shares a powerful case study of a founder who used the rationale framework to double their offer—by helping the buyer see the long-term potential. “They shrugged and said, ‘We’re not paying you enough.’ That’s the Jedi mind trick.” – Mark What Makes an M&A Outcome Truly Successful (23:31) Success isn’t just the highest purchase price. It’s achieving the intent of the transaction—alignment, culture, growth, and impact. “Think beyond the number. Think about the next chapter.” – Mark Final Thoughts: Hiring the right advisor can unlock enormous value—but only when paired with clear leadership from the CEO. This episode offers a roadmap for founders preparing to sell, highlighting how to build an aligned, expert team while maintaining ownership of the process. Deals aren’t just financial—they’re personal, strategic, and long-term. The right partner makes all the difference.
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    26 mins
  • COLADV MM M&A - 030: Questions to Ask Buyers

    COLADV MM M&A - 030: Questions to Ask Buyers
    Feb 20 2025
    29 mins
  • MM M&A - 028: Strategic Exit Planning for Equipment Leasing and Finance Companies

    MM M&A - 028: Strategic Exit Planning for Equipment Leasing and Finance Companies
    Oct 10 2022
    In this episode, we discuss strategic steps for Equipment Leasing and Finance companies as they grow and evolve. The leadership of some of these businesses may decide to remain a certain size and complexity and be “ lifestyle businesses”, providing healthy cash flow to the owner(s) while they continue to run the business. However, other options exist, and exiting the business for a favorable multiple to a bank or other buyer can be an excellent strategy, the dream plan for many entrepreneurs.  In this interview, we interview Bob Rinaldi and discuss the potential to grow and leverage a business to realize a win-win exit strategy.  This episode is a great follow-up to our previous show, Start Early & Exit Right, as we dive deep into many of the concepts of M&A rationale. What’s unique about this episode is that it is geared toward a specific target audience, our friends in the Equipment Leasing and Finance (ELF) industry. In this episode we cover: How partners such as Rinaldi Advisory Services (RAS) and Colonnade work with Equipment Leasing & Finance (ELF) companies to prepare for a successful sale (1:00)What are the biggest challenges for the independents as they look to be “bank ready” for an acquisition? (4:00) What are some of the biggest challenges for banks pursuing an acquisition of an equipment leasing company? (9:30)What determines the level of a premium in the sale price that an ELF company can expect? (20:00)What has M&A activity looked like in recent years and what are the prospects? (23:00)What about Private Equity buyers in this space? (26:30) How partners such as Rinaldi Advisory Services (RAS) and Colonnade work with Equipment Leasing & Finance (ELF) companies to prepare for a successful sale (1:00) Bob: My practice has evolved around three target audiences in the equipment leasing space. About 60% of my clients are independent leasing (ELF) companies that I work with through the Confidential CEO Resource℠ model. This is multi-year exit strategy planning. Whether the company exits or not is not important. The idea is to get them from point A to point B so they’re prepared if that time comes. The second part of my practice is working with banks, predominantly community banks who are looking to get into the ELF space. Third, I work with a handful of service providers in the industry, as well. Rinaldi Advisory Services (RAS) offers the Confidential CEO Resource℠ (CCR) as a robust, full-scope advisory service that provides clients with a broad base of support for long-term strategic management. RAS works with CEOs and Principals to provide meaningful analysis and actionable insights. The aim is to help ELF senior management arrive at strategic and tactical decisions geared toward managing growth as well as operational and financial efficiencies. Colonnade has deep experience in the ELF industry. Colonnade is a leading investment banking firm that has completed over $9 billion in M&A transactions for clients in the business and financial services industries. Colonnade has advised many companies in the EFL sector on strategic transactions. Please see our Quarterly Updates on the ELF industry here. What are the biggest challenges for the independents as they look to be “bank ready” for an acquisition? (4:00) Bob: The biggest challenge is predominantly that these founders/owners are very much entrepreneurs. They started the business. They’re very much involved in the everyday transactional nature of their business. They don’t have the time to gain the perspective to look at their company objectively and determine what needs to happen to be a better company from a non-transactional standpoint or to be a better company for the purpose of acquisition. Jeff:  Let’s drill down a little bit on some of the biggest challenges for the independents. There’s size and scale, where are you today and where are you going? Banks are the natural resting home for specialty finance companies, and ELF companies are such a great asset class for banks in particular. Obviously, they’re a number of large independents, but from the bank’s perspective, what are the other things you see where companies need to focus? Is it finance and accounting? Is it operations? Is it servicing? Bob: Yes. Yes. And yes. It’s really all those things. But even before you get to that, let’s look at the business and find components within the business that definitely will never, ever fit in a bank. I’m able to identify those things. You then have to decide what to do with those things. Do I jettison those things completely? Do I sell those off? Do I break it outside of the company and put it in a separate entity so that what is left is sellable and simple to understand? Compare that to a buyer looking at the company and thinking, “I like this, I like this. I hate that. Therefore, I’m not doing it [the acquisition].” For example, say that there is a heavy services component of the (ELF) business;...
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    30 mins
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