Do You Actually Want to Be a Deal Maker?

I spend most of my time on this podcast talking about why deals are the single most powerful growth accelerator for businesses. I've been doing deals for over 35 years. I train people in negotiating and deal making. So it might seem a little counterintuitive that I'd devote an entire episode to telling you why maybe you should not be a deal maker.

But I think this conversation matters, because the flip side of understanding why deal making might not be for you is understanding exactly what it takes to succeed at it. Self-knowledge is the starting point for every good deal, and that includes the deal you make with yourself about how you want to build your business and live your life. Whether you decide to pursue deal-driven growth or focus on other paths, the most important thing is making that choice from a place of clarity rather than assumption.

SOMETIMES YOU HAVE TO PUSH THROUGH

The nature of deals, especially when you are working on more than one at a time, can be all-encompassing. They take enormous amounts of time, effort, and focus. I'll be transparent about my own experience. I recorded this episode at the end of December with multiple year-end closings on the table. My team was stretched. I was under the weather. We still had significant work to complete before December 31st, including detailed disclosure schedules for several asset purchase deals.

That's the reality of deal work. Even when the finish line is in sight, critical tasks remain. Disclosure schedules, for example, require sellers to provide detailed representations and warranties covering everything from contracts and employee issues to regulatory matters and taxes. If you don't properly complete those schedules, you increase your risk of being in breach, which could trigger indemnity obligations down the road.

The broader point is this. Even with the right team, the right systems, and decades of experience, there will be moments when deal work demands that you push through. For people doing it for the first time or without experienced advisors, those moments can be even more intense. If you are someone who cannot handle that kind of periodic intensity, deal making may not align with how you want to run your business.

RISK IS PART OF THE GAME

The second major reason deal making may not be for you comes down to risk tolerance. No matter how thorough your due diligence, no matter how experienced your team, no matter how well-structured your deal, some deals will fail. They will blow up. They will underperform. They will die before closing or go sideways shortly after.

Talk to any highly successful deal maker and they will tell you about the ones that didn't work out. That's the nature of it. If you are an entrepreneur, you already take risks in your business. Deal making introduces additional layers of risk on top of those. There is a spectrum, of course. You can moderate the types of deals you pursue, the pace at which you pursue them, and the level of due diligence you apply. But the inherent risk never goes away entirely.

I have a deal going on where the buyers genuinely want to complete the transaction but are extremely risk averse. We are structuring protections and guarantees to get them comfortable, while making sure those provisions don't overburden my client. That dynamic is a real-world illustration of how someone's risk tolerance, or lack of it, can directly affect whether a deal gets done. If doing deals would keep you awake at night or affect your health, it may not be worth it for you. And that's a completely legitimate conclusion.

MAYBE YOUR SUPERPOWER IS ORGANIC GROWTH

I have said many times on this podcast that every single company, regardless of industry, size, or capital, can find a deal that would help grow the business. But that doesn't mean every company should pursue deals. If you are already very successful and growing significantly through organic means, through exceptional marketing, sales, or talent acquisition, adding deals to the mix could actually become a distraction from what you do best.

I've been in that position myself. I've had years where my planning identified twenty initiatives worth pursuing but capacity only allowed for eight. You make choices. Sometimes the smartest choice is to double down on what's already working rather than diversifying into deal making.

Now, I believe there is vulnerability in relying solely on organic growth. Having multiple growth strategies, like a diversified stock portfolio, reduces risk for your company overall. But not every business leader needs to be the one driving the deal strategy. You might hire the right people, bring in experienced partners, or build a management team that handles deal activity while you focus on your highest and best use.

SELF-KNOWLEDGE MATTERS MORE THAN AMBITION

This is where I always come back to my core philosophy. Before you decide whether to pursue deals, you need absolute clarity on what you want from your business and your life. The CPR tool from my Authentic Negotiating book, which stands for Context, Purpose, and Results, is designed for exactly this kind of assessment. You can apply it to a specific negotiation or to your entire life. It helps you get clear on what matters most.

When I launch my dealmaker retreats, the first thing we will do is visioning work. That's because I want people to hold their deal ambitions in the context of what they actually want to achieve in their lives. We should be creating businesses to create the lives we want. We should be doing deals to create the lives we want. And if the life you want doesn't include the demands of deal making, that's a perfectly valid answer.

Maybe you're later in your career and you'd rather travel, spend time with family, or play golf than take on the intensity of acquisitions. Maybe you've considered the risks of not diversifying your growth strategies and you've concluded that you'll be fine. Those are legitimate, self-aware decisions. Nobody has to be a deal maker. The important thing is that you're choosing consciously.

WHAT IT TAKES TO BE A DEAL MAKER

If you flip everything I've covered so far, you get a roadmap for what successful deal making requires. You need the willingness to push through intense periods when closings stack up and timelines compress. You need a tolerance for risk that allows you to move forward knowing that some deals will not work out. You need to honestly assess whether deal activity is the best use of your time and energy, or whether building a team that handles it is the smarter path.

You also need the right resources. Experienced attorneys, investment bankers, accountants, and consultants who have been through these processes before can dramatically reduce the learning curve and the scrambling. In the beginning, before you've built those relationships and systems, deal work will be harder and more stressful than it needs to be. One of the highest-value investments a prospective deal maker can make is assembling that team early.

And you can evolve. Being a deal maker is not binary. Just like there are born entrepreneurs and situational entrepreneurs, there are people who become deal makers because the timing is right, because an opportunity appears, because they've built the foundation in other areas of their company, or because their mindset shifts. The beginning of any year is a natural time to ask yourself whether this is the year to start doing deals, to do more deals, to do bigger deals, or to focus your energy elsewhere entirely. Both answers are correct, as long as you're making the decision from a place of self-awareness.

This conversation connects to themes I've explored with Herman Dolce about how the people around you filter advice through their own risk tolerance, and with Pete Mohr about how exit planning and freedom are deeply connected to knowing what you want from your business. The throughline is always the same. Clarity first. Strategy second. Deals when they serve the life you're building.

Listen to the full episode of DealQuest Podcast: Available on all major podcast platforms

FOR MORE ON COREY KUPFER
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https://www.coreykupfer.com/

Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.

Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!