Episode 396: Do You Actually Want to Be a Deal Maker with Corey Kupfer

From year-end deal crunches to honest conversations about risk tolerance and self-knowledge, Corey Kupfer makes the candid case for why deal making may not be for every entrepreneur, and what it actually takes if you decide it is.

In this remastered DealQuest solocast, host Corey Kupfer draws from his own experience managing multiple year-end closings while stretched thin to walk through three reasons why deals may not align with every business leader's goals or temperament, and how the flip side of each reason reveals the roadmap for those who do want to pursue deals.

WHAT YOU'LL LEARN

In this episode, you'll discover why even experienced deal teams face periods of all-encompassing intensity, how risk tolerance shapes whether and how you pursue deals, and why some entrepreneurs are better served by doubling down on organic growth. Corey explains how the CPR tool from his Authentic Negotiating book can help you assess whether deals belong in your growth strategy, and why the distinction between born deal makers and situational deal makers matters.

THE HONEST CASE FOR SELF-ASSESSMENT

Corey acknowledges the counterintuitive nature of a deal-making advocate telling listeners they might not want to be deal makers. But the premise is grounded in something he returns to throughout his work. Self-knowledge matters more than ambition. The decision to pursue deal-driven growth should come from clarity about what you want, not from external pressure or assumptions.

He connects this to the CPR tool from his Authentic Negotiating book, which stands for Context, Purpose, and Results. The CPR framework applies as powerfully to the question of whether deals should be part of your growth strategy as it does to any specific negotiation. Corey also previews his dealmaker retreats, which will begin with visioning work before any deal strategy is discussed.

KEY INSIGHTS

Deal work is periodically all-encompassing. Corey shares his experience managing multiple year-end closings while sick, with his team stretched. He walks through disclosure schedules in asset purchase deals, where sellers must provide representations and warranties covering contracts, employees, regulatory matters, and taxes. Getting these wrong risks breach and potential indemnity obligations.

Risk tolerance is a prerequisite. Every successful deal maker has deals that fail or underperform. Corey shares a live example of risk-averse buyers requesting protections that could burden his client. If deals going wrong would affect your sleep or health, the personal cost may outweigh the benefit.

Your highest and best use may not include deal making. Some entrepreneurs generate exceptional results through organic growth. Adding deals could dilute their greatest strength. Corey compares growth diversification to a diversified stock portfolio but notes you can hire the right team to handle deals while you focus on your strengths.

Being a deal maker is not binary. There are situational deal makers who evolve into the role because the timing aligns, an opportunity appears, or their mindset shifts. The question is whether this is the right time for you.

Perfect for entrepreneurs weighing whether deal-driven growth aligns with their goals, business owners considering M&A or partnerships, and anyone interested in an honest self-assessment framework before committing to a deal strategy.

FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/beadealmarker

FOR MORE ON COREY KUPFER:
LinkedIn: https://www.linkedin.com/in/coreykupfer/
Website: https://www.coreykupfer.com/ 

Episode Highlights with Timestamps:
[00:02:12] - Solocast opens with the counterintuitive premise of why you should not be a deal maker
[00:04:53] - Why deal work can be all-encompassing and the demands of year-end closings
[00:06:32] - Disclosure schedules in asset purchase deals and why they matter
[00:10:25] - The reality of pushing through fatigue and intensity
[00:11:57] - The inherent risk of deal making and why some deals will always fail
[00:14:01] - Live deal example with risk-averse buyers requesting protections and guarantees
[00:14:54] - Organic growth as an alternative path and when deals become a distraction
[00:15:53] - Superpower and highest and best use
[00:18:25] - Self-knowledge as the foundation and the CPR tool from Authentic Negotiating
[00:19:00] - Dealmaker retreats and why they start with visioning
[00:21:02] - What it takes to be a deal maker and the concept of situational deal makers

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

Show Description:
Do you want your business to grow faster? The DealQuest Podcast with Corey Kupfer reveals how successful entrepreneurs and business leaders use strategic deals to accelerate growth. From large mergers and acquisitions to capital raising, joint ventures, strategic alliances, real estate deals, and more, this show discusses the full spectrum of deal-driven growth strategies. Get the confidence to pursue deals that will help your company scale faster.

Related Episodes:
Episode 326 - Herman Dolce: How People Around You Filter Advice Through Their Own Risk Tolerance
Episode 330 - Pete Mohr: Building Enterprise Value and Exit Readiness
Episode 323 - Holiday Solocast: Year-End Completion and Clearing Exercise for Entrepreneurs
Episode 324 - Sejal Lakhani-Bhatt: Entrepreneurial Mindset, Vulnerability, and Authentic Leadership

Keywords/Tags:
deal making mindset, risk tolerance in deals, deal maker self assessment, organic growth vs acquisitions, deal-driven growth strategy, entrepreneur risk tolerance, when not to do deals, self-knowledge in business, authentic negotiating CPR tool, situational deal makers, disclosure schedules, highest and best use, deal-driven growth