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From Negotiation Coach to AI Power User

From Negotiation Coach to AI Power User

How Boris Pfeiffer Uses Custom GPTs to Scale Wisdom at Work

Bernard Desarnauts
May 20, 2025 • Estimated Reading Time: 4 minutes

MEET TODAY’S GUEST

Boris Pfeiffer, Riddle.com Founder

Boris built Riddle.com into a go-to platform for interactive content—used by everyone from the BBC to the Fiesta Bowl. But beyond the SaaS world, Boris and his wife run a two-person publishing business, where AI is quietly transforming how they operate and scale.

Boris Pfeiffer’s first AI experiment? A poem in ChatGPT. But within weeks, he was spinning up powerful GPTs trained on everything from FBI negotiation tactics to marketing psychology. These custom models now help him draft persuasive emails, brainstorm strategy, and tailor ad copy across two very different companies—all without touching a line of code.

“A good engineer with AI becomes two engineers. A good content producer becomes two content producers.”

- Boris Pfeiffer

The magic, he says, isn’t just in what AI writes—it’s in how it helps you think.

Custom Build ROI

Four Use Cases Boris Called Out

Internal Negotiation Coach
Based on Chris Voss’s methods, rewrites emails and preps tough conversations.
Marketing Copy Generator
Combining brand docs + Rory Sutherland’s talks to shape high-converting language.
Brainstorming Assistant
Boris uses voice chat to simulate real-time coaching and unblock ideas.
Angry Email Fixer
Input your rant, get a calm, persuasive version back in seconds.

Playbook for SMB Owners (3 Steps)

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Playbook for SMB Owners (3-Step Version)

Rank Your Drudge Work. List weekly tasks; circle ones with templates or long copy. Thomas started with proposals because they were daily and measurable.
Run a Micro-Pilot. Copy last week’s proposal bullet points into ChatGPT or Gemini. Record drafting time vs. the old 3-hour average.
Build a Re-Use Library. Thomas noted the need for “a library of data…boiler-plate language.” A shared folder of gold-standard clauses lets AI remix quality, not junk.

Change Management: Thomas’s View

“Nobody on my team is afraid of being replaced. What we talk about is how we each double our output without doubling our stress.”

- Boris

Rather than pitching AI as a threat, Boris frames it as a multiplier. That’s helped shift curiosity into action—even among skeptics.

Staying Current Without Losing Your Mind

Boris admits it’s hard to keep up. His solution? Start small.

Add a short “AI tip of the week” to internal comms.
Try one experiment a week in your workflow.
Track what actually saves time (not what’s shiny).

What’s Next on His Radar

Auto-filled timesheets – tools watch work patterns and draft entries.
Design co-pilots – AI proposes pipe sizes and grading; engineers approve.
Reg-scan bots – upload a city ordinance, get a one-page delta sheet.

Try This Before Friday

Prompt: “You are a negotiation expert trained in the Chris Voss method. I’m frustrated with a client who missed a deadline. Rewrite my message to preserve the relationship while being firm on next steps.”

Why it matters: Boris uses this exact flow to manage vendor and customer relationships with less stress and more impact. If you’re spending more than 15 minutes writing tough emails, this saves time and energy.

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