Jeff Macpherson

Ep. 275 | AI Won’t Fix Your Business. It’ll Expose It.

Podcast Episode
August 26, 2026•3 min read
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What happens when you add AI to a business with bad systems?

You don’t magically get a better business. You may just break things faster.

Jeff MacPherson, CEO of Cloud37, joins Matt Meehan and Luigi Rosabianca to talk about what AI can actually do for small businesses—and where founders keep getting it wrong.

Jeff has spent years building tech, including an early Instagram automation platform that sent more than a billion messages before Facebook shut it down. Today, he helps companies turn what their best people know into repeatable systems that can scale.

The big lesson? Stop chasing the newest AI tool. Fix the way your business works first.

🍸 What you'll hear in this episode:

  • Why AI exposes bad processes instead of fixing them

  • The onboarding mistake that quietly slows down growth

  • Why standard questions make AI work better

  • How to pull knowledge out of your best employees’ heads

  • Why human adoption is often harder than the tech

  • How one financial firm improved sales and service with the same system

  • Why AI may expose fake experts faster than real ones

  • The reason “white glove” service still matters

  • Why relationships may become more valuable as AI gets better

  • What losing an entire company to Facebook taught Jeff about platform risk

  • Why founders should build systems—not depend on one AI model

👤 About our Guest:

Jeff MacPherson is the CEO of Cloud37, where he helps businesses turn internal knowledge and proven processes into AI-powered systems that can scale. He previously built one of the earliest Instagram messaging automation platforms and has spent more than a decade building technology businesses.

🎧 Why Listen:

AI can make a good process faster. It can also make a bad process fail faster.

Before you automate everything, figure out what actually works, make it repeatable, and keep the human relationships your competitors can’t copy.

Know a founder who keeps buying AI tools but still runs the company from their inbox? Send them this episode. Then follow The Liquid Lunch Project so you don’t miss the next conversation.

🔗 Links + Stuff

🔔 Enjoyed the episode?

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If this episode helped, a quick rating or review goes a long way. It helps the show reach more business owners who actually care about getting this right.

🎧 Listen or watch The Liquid Lunch Project

Available on all major podcast and video platforms:

• Official site: https://theliquidlunchproject.com
• Apple Podcasts: https://podcasts.apple.com/us/podcast/the-liquid-lunch-project/
• Spotify: https://open.spotify.com/show/12HPEDMmsbfsp8tHt5LiZJ
• Audible: https://shorturl.at/6j4vz
• YouTube (full episodes + clips): https://www.youtube.com/@theliquidlunchproject

📬 Want more than just the podcast?

Every Friday, we publish The Weekly.
A fast, smart rundown of what actually matters in finance, tech, small business, and the economy…without the noise.

Subscribe here: 👉 https://theweeklyfromshieldadvisory.substack.com/

💼 Need funding or working capital?

If today’s conversation raised questions about capital, cash flow, or financing options, you can schedule a conversation with our sponsor, Credit Banc.

Credit Banc helps business owners make sense of their options and move forward with a clear plan, without pressure or guesswork.

👉 Book a free 15-minute call here: https://tinyurl.com/3dh9vy86

📲 Connect with the hosts

Follow along for behind-the-scenes clips, commentary, and things that don’t make it into the episode.

• Matt Meehan: https://www.instagram.com/matthew.r.meehan
• Luigi Rosabianca: https://www.instagram.com/luigi_rosabianca
• The Liquid Lunch Project: https://www.instagram.com/theliquidlunchproject/

💬 One last thing

Know a business owner who would appreciate this conversation?
Send them the episode. That’s how this show grows.




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