When I started my AI Journey, I once spent 4 hours automating a 5-minute task. Here's what I learned.
AI isn't magic. It's messy. An expanding sea of overlapping tools, outlandish claims, and no clear guidance on which one to use or how to use it. I tried various tools, mangled prompts, broke APIs, got frustrated, and wasted an afternoon on a simple report.
But I learned the system's limits and how to actually wield the tool. Adoption requires patience and a willingness to fail – because each failure holds a key lesson. Just like learning to ride a bike as a kid: the key lessons were gleaned from the falls, not the victories.
What's your biggest AI fail?
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I’m going to say what most sellers won’t: AI has made prospecting and earning executive meetings too easy.
After 25 years in sales, I’m operating at the highest level of my career — not because I work more. Because I'm resourceful and use every tool at my disposal.
Here’s my exact workflow that’s driving nearly a 100% success rate landing executive meetings in complex organizations:
Sales Navigator pulls every executive I should engage.
I create my own lists for newsletters and webinar outreach. Recently, a customer made a huge purchase that nobody on my team even spoke to; turned out, they were on all my webinars.
Here are the prompts powering 80% of my prospecting:
Prompt #1 – Executive Intelligence Compression
Analyze this executive’s website, annual report, earnings call transcript, and LinkedIn activity.
Summarize their top 3 strategic priorities, current challenges, tone of voice, and recurring language patterns. Identify 2 potential blind spots or emerging risks they may not be explicitly addressing.
Prompt #2 – The 2-Sentence Hook
Based on this executive’s priorities and tone, draft a 2-sentence hook that signals relevance, insight, and urgency — without sounding salesy. Use their language style.
Prompt #3 – The Surgical Email
Write a concise 2-paragraph outreach email (under 120 words) aligned to their mission and strategic priorities. Make it feel written specifically for them. Include a subject line optimized for open rate and curiosity.
Prompt #4 – The Board-Level Angle
If I were presenting to this executive’s board, what metrics and outcomes would matter most?
Reframe my value proposition in board-level language.
Prompt #5 – Objection Pre-Handling
List the 5 most likely reasons this executive would ignore my outreach.
Then rewrite my message to neutralize those concerns preemptively.
Prompt #6 – Account Expansion Map
Identify 5 adjacent executives inside this organization who would logically care about this initiative and explain why.
What used to take me 2–3 hours per account now takes 15 minutes.
AI didn’t replace the craft.
It amplified it.
It sharpened my pattern recognition.
It accelerated my preparation.
It increased my precision.
Most sellers are still blasting generic emails.
Meanwhile, AI lets you speak directly to what keeps an executive awake at night — in their own language — at scale.
If you understand their perceived risk of change, and you understand their why, you can influence anything.
The organizations people call “uncrackable”?
They’re just under-researched.
If you’re in sales and you’re not building AI into your daily workflow, you’re not competing against other reps.
You’re competing against augmented operators.
What’s one AI workflow that materially changed your performance?
If you want my entire playbook, check out my new book "Moneyball Sales."
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Shifting perspective doesn't mean giving up your view. It means being willing to see what's true from where someone else is standing. That one move can change a conflict into a conversation. What's a perspective shift that surprised you lately? Sha...
https://t.co/zkMA5zDRBZ
I genuinely don't understand why everyone isn't using this yet
Andrej Karpathy, a co-founder of OpenAI, posted a simple idea that hit 16 million views: stop using AI to write code, use it to build a second brain.
You point Claude Code at a folder, drop in any source, an article, a transcript, a PDF, and Claude reads it, links it, and files it into a living wiki of everything you know. It compounds like interest, the more you feed it, the smarter it gets.
Here's the whole thing:
> Install Obsidian, create a vault, open it in Claude Code
> Paste Karpathy's wiki idea file and tell Claude to build it
> Claude makes three folders: raw for sources, wiki for its pages, a CLAUDE.md that runs it
> Drop any source into raw and say "ingest this"
> Ask questions across everything, forever
Five minutes to set up, and you never start from a blank chat again.
Full step-by-step guide with Claude and Obsidian, link below.
Bookmark this
Stop paying your team to take notes & track action items. Let AI do this for you. DM me with the keyword “AI Meetings” for a full breakdown of the Top 5 AI Meeting Assistants. For the exact AI workflow, see the full post on LinkedIn: https://t.co/54wEmthBVL
AI won't replace your employees. But a competitor using AI will replace your business.
The threat isn't a robot taking jobs. It's the firm across town doing in 1 hour what takes your team a week.
Adapt or become obsolete.
What's your biggest AI fear?
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