2025 M&A Lessons #3 - "Keep Your Heart 3Stacks, Keep Your Heart"

“Keep your heart, Three Stacks, keep your heart

Ayy, keep your heart, Three Stacks, keep your heart

Man, these [Sellers] smart, Three Stacks, these [Sellers] smart Play your part, play your part"

- Andre 3000 [bracketed text added]

“How many LOIs did you send last month? If the answer isn’t 10 or more, you’re not serious about buying a business. Most first-time Buyers waste months waiting for the perfect deal to appear, or they let Brokers dictate the timeline. That’s not how successful Buyers operate. The real players? They go on offense. They send LOIs on Day 1, before anyone else has a chance to bid. And they send at least 10 LOIs every month to build momentum and create options.”

- Elliott Holland on LinkedIn early in 2025

What if we told you that both of these quotes reveal the same lesson for those exploring an M&A transaction – “keep your heart”? As you approach the big, long-term commitment of buying or selling a business, keep your options open, proceed with caution as you’re “courting” prospects, and don’t get attached before the ink has dried.

The first quote is from Andre 3000’s legendary opening verse on “Int’l Players’ Anthem (I Choose You).” This culturally iconic song actually belongs to the rap duo UGK, but guest artist Andre 3000 a.k.a. “Three Stacks” (and his iconic verse) steal the spotlight. They emerge as the unquestionable stars of the track (and the storyline). What’s the plot? As Three Stacks delivers his lyrical masterpiece in his unique conversational style, we learn that love and monogamy (and apparently, marriage) are on his agenda. Our lovestruck hero professes his love for a woman and desire to forsake all others for her. In response to these declarations, the rest of the artists on the track warn him to think twice about giving up his freedom based on his emotions - “re-consider, read some liter-ature on the subject. You sure? F*** it.”

The second, no less engaging, quote is from Elliott Holland of Guardian Due Diligence, our go-to financial due diligence/QOE provider. He describes the proactive, opportunistic approach required to succeed at searching for and acquiring a business. Elliott flags the common pitfall of “waiting for the perfect deal to appear.” We see this often, including in the 2025 client deals for which we joined forces with Elliott.

One result of “waiting for the perfect deal to appear” – when a searcher “finally” discovers what they think is the perfect deal and their LOI is accepted (an amazing feeling!), that searcher can develop a deep attachment to that deal. This reaction is understandable and natural but, for a deal only under LOI, can lead to heartbreak.

In the concise, punchy way that only good hip-hop can, Andre 3000’s lyrics capture the hidden danger that our M&A clients face. We don’t promote International Player’s Anthem’s attitudes toward women or its general message of distrust toward relationships. When buying or selling a business, however, the iconic line “keep your heart Three Stacks...these girls are smart...” provides a critical reminder to our clients. Just substitute “girls” with “broker” or “seller” (or “buyer”). Sellers and brokers can be “smart” (i.e., slick, strategic, even misleading), enticing buyers to enter into a long term relationship with the target company based on false pretenses.

Until your good friends (legal and financial advisors) have vetted your attractive relationship interest, we urge our clients not to get emotionally attached!

To be fair, while we mostly do buy-side representations, we also do sell-side and this principle proves useful for Sellers too. Keep your heart – don’t start counting (and spending) your money until the papers are signed and the wire hits.

This ties into, but differs slightly from M&A Lesson #4. In that post, we discussed emotional regulation and intelligence as valuable skills in general. In Lesson #3, Andre 3000 and Elliott Holland teach us the value of specifically not making a deal your end-all-be-all until you are sure. In Lessons #2 and #1, we’ll provide specific ways you can get more sure -- diligence and QOE.

Disclaimer. The contents of this article should not be construed as legal advice or a legal opinion on any specific facts or circumstances. Your viewing and/or use of the contents of this article do not create an attorney-client relationship with Cadet Legal. The contents are intended for general informational purposes only, and you are urged to consult with counsel concerning your situation and specific legal questions you may have.