The Deal Fell Through... and I’m Relieved?!

Plus some AI Strategies founders can implement

Author

Joshua Clear
May 31, 2025

In partnership with

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Dave Hamilton & Shannon Jean – Two seasoned entrepreneurs who've built, scaled, and sold multiple businesses. These aren’t your typical "Twitter thread" gurus—they’re the guys who’ve actually been in the trenches. Think: business therapist meets startup playbook.

🎙️ SNAPSHOT

Ever felt oddly relieved when a big deal fell through? In this brutally honest episode, Dave opens up about a major acquisition deal that crashed and burned… and why he’s weirdly thrilled about it. Plus: time-blocking hacks, AI calendar wizardry, and a genius way to automate chaos after a 500-person mastermind explodes overnight.

💡 KEY TAKEAWAYS

  • Sometimes a dead deal is a bullet dodged. Dave’s relief after an 18-month acquisition collapse revealed deeper concerns about control, speed, and decision-making in partnerships.

  • AI is your executive assistant now. Lydia Davey from Attentio PR uses ChatGPT to prioritize tasks, block her calendar, and even tell her what to outsource—using just a pic of her to-do list 🤯.

  • Don’t emotionally commit to a deal until the check clears. Veteran wisdom: The deal isn't real until it's done. Hope is not a strategy, and "time kills all deals."

  • Manual before scale. Shannon's approach to his 500-member mastermind proves that doing things manually first reveals the friction points you must systematize later.

  • Time-blocking is the antidote to chaos. Using AI to batch schedule calls saved Shannon from drowning in 15-min call requests. Pro tip: Only open up 90 minutes per day to maintain sanity.

🛠️ TOOLS, WEBSITES, RESOURCES MENTIONED

  • 🛡️ NordLayer – Enterprise-grade security for startups and scale-ups. VPN + access control + threat shield. Zero-trust security model, built for modern remote teams.

  • 🛍️ Shopify – $1/month trial with built-in AI tools to help you build, market, and sell anything online. Used as a metaphor for removing excuses like “What if I don’t know how to code?”

  • 📅 ChatGPT (with screenshots or ICS files) – Use multimodal prompts to manage your schedule, prioritize tasks, and even sync multiple people’s historical activity across formats (like combining Google Sheets and .ics calendar files).

💼 BUSINESS IDEAS & OPPORTUNITIES

  • AI-Powered Calendar Concierge Service – For overwhelmed founders, offer screenshot-to-prioritization service using ChatGPT + Notion + Google Calendar.

  • Acquisition Advisor for Small Biz – Specialize in navigating emotional, legal, and control-based landmines in 6- to 7-figure deals.

  • Mastermind-to-Consulting Pipeline – Mimic Shannon’s strategy: low-ticket group → discovery call → upsell into high-touch coaching. Just be ready when it scales fast.

🧠 LIFE HACKS

  • "Screenshot your chaos." Instead of overthinking priorities, screenshot your task list or calendar, dump it into ChatGPT, and let it optimize your day.

  • The 90-Min Rule. Only allow calls or coaching sessions during a fixed 90-minute window per day. Forces prioritization and prevents burnout.

💰 BEST MONEY-MAKER IDEA

The AI time-blocking concierge is ripe for monetization. Everyone is overwhelmed. Turn this into a $99/month service targeting solo founders, consultants, and coaches. Minimal overhead. Maximum ROI.

  • Shopify powers 10% of U.S. e-commerce. That’s not just a side-hustle tool—it’s the backbone of digital commerce.

  • 500 mastermind signups = 125 hours of calls. Shannon’s growth illustrates how fast digital communities can scale—and how quickly they become operationally painful without systems.

🔑 ACTIONABLE STRATEGIES

How to Use AI for Calendar + Task Management:

  1. 📝 Write your to-dos on paper or planner

  2. 📸 Snap a photo

  3. 🧠 Prompt ChatGPT: “Here’s my list. How do I prioritize, what can I outsource, and how should I block my time?”

  4. 🗓️ Upload your calendar screenshot or ICS file

  5. 📍 Let ChatGPT suggest your optimized day or week

  6. 🔁 Refine weekly for continuous improvement

📚 BOOKS MENTIONED

None directly mentioned, but the episode’s vibe screams:

  • The E-Myth Revisited (systematize before scale)

  • Built to Sell (understand what buyers care about)

🚀 GROWTH HACKS & CHEAT CODES

  • Use ChatGPT’s multimodal capabilities to synthesize across formats—like matching .ics files with Google Sheets for shared event tracking.

  • Sponsorship stacking – They subtly but effectively plug both Shopify and NordLayer with strong calls-to-action and value-driven metaphors. Pay attention to that if you're monetizing your pod/newsletter.

📝 EXECUTIVE SUMMARY

This week’s episode of Business Brain is part therapy session, part masterclass. Dave shares how a failed 18-month acquisition brought unexpected clarity and renewed control over his business. Shannon walks us through real-world scaling pains and how AI is helping him regain control over his time. The underlying thread? Modern entrepreneurship requires tech fluency, self-awareness, and systems. Whether you're selling a business, growing a community, or just trying to survive Monday—this episode delivers tactical wisdom you can use right now.

🎯 Common Theme:
Control vs. Chaos. Whether it's selling your business or scheduling your day, the theme this week is about reclaiming power—through self-awareness, smarter systems, and a dash of AI magic. 💼⚙️🤖

Full episode we got our notes from: