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🌟 Zelensky vs. Trump: The Art of Losing a Deal (Issue 127)
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🌟 Zelensky vs. Trump: The Art of Losing a Deal (Issue 127)

The Top 10 Biggest Red Flags when Closing a Business Deal

Gaslighting, lying, bullying, threatening, belittling, and generally toxic behavior.

We’ve all endured some lose-lose moments in our working relationships when deals go sideways, conversations become hostile, and you wonder if you can keep working together.

  • Those red flags in an initial client meeting that you shouldn’t have ignored.

  • A friendly customer who later turns hostile and demanding.

  • The deal negotiation that is starting to feel like it will be a terrible idea to accept.

I’m happy to have Anna Codina as my co-host for this episode (and hopefully all future episodes). Anna and I have known each other for many years, and she has been a solopreneur for most of her working life. We co-hosted a previous podcast together with another friend, Trip O’Dell, which was called the Brave New Workforce.

Anna Codina

In this episode, Anna and I discuss why so many of us had an immediately familiar and bad feeling as we watched Volodymyr Zelenskyy, the current president of Ukraine, get pulled into an unpleasant deal negotiation (regarding a mineral deal and cease-fire negotiation with Russa) that went sideways in the Oval Office on Feb 28th, 2025 with the U.S. president, Donald Trump.

In just a few minutes, many red flags popped up in this political meeting that typically would take weeks or months to emerge after working with a troubling business client. Anna and I have both experienced many of these issues and learned some painful lessons.

Hit play to listen to our conversation about identifying these red flag issues and how you can avoid them as a solopreneur business owner.


10 Red Flag Moments from the Oval Office

  1. They try to control the narrative from the beginning.

  2. The goalposts keep moving.

  3. A positive, upbeat beginning turns into a rapid, hostile tone switch.

  4. They start asking you to justify your worth and putting you on the defensive.

  5. They “dangle the carrot” of the future, wonderful things.

  6. Nothing they discuss is set in stone (e.g., everything is vague and fuzzy).

  7. They try to force unrealistic timelines.

  8. They criticize without offering details or solutions.

  9. They want you to “work for exposure” (i.e., you should feel lucky to have the deal).

  10. They trash-talk past partners, contractors, employees, etc.

Scroll up, hit play, and listen to our entire conversation. Comment below if you have a story about a red flag moment with a client or potential customer.

  • What did you learn from it?

  • What advice would you give others?

Leave a comment


Larry Cornett is a Freedom Coach who works with ambitious professionals to help them reclaim their power, become invincible, and create new opportunities for their work and lives. Do more of what you love and less of what you hate! Check out his new Invincible Solopreneurs Daily Journal!

Anna Codina is a peak performance coach who helps busy owners detach from work to live better personal lives. Are you feeling overwhelmed, burnt out, or struggling to find that elusive work-life harmony? You're not alone. Her coaching philosophy is simple: Focus on your strengths, not your weaknesses. Get unstuck in 15 mins!

Larry Cornett and Anna Codina
Larry Cornett and Anna Codina

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