Why Your AI and Automation Projects Keep Failing (And How to Actually Make Them Work) | Lazy Leverage #66

28 snips

Jul 24, 2025

In this insightful discussion, Brian Wilson, a retired Marine Corps Major and head of Sagan's Knowledge and Automation group, reveals why businesses often fail in AI and automation projects. He emphasizes the need for simplicity before complexity, advocating for straightforward solutions over expensive tech. Brian shares his experiences in training sessions, highlighting how focusing on fundamental skills beats shiny tools. The conversation also introduces "skill sprints," aimed at building practical automation habits through teamwork and daily challenges.

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INSIGHT

Reality Check on AI Advice

Most AI and automation content creators lack real business problem-solving experience.
Recognizing the actual problem often takes much longer than expected, requiring human skills and patience.

ANECDOTE

Solving Real Problems Live

Brian helped a business owner clarify their biggest problem after 23 minutes of questioning.
They built an automation in 37 minutes to solve the key issue.

ADVICE

Duct Tape and Zip Ties Philosophy

Use simple, quick 'field expedient' solutions before expensive, complex ones.
This approach helps test effectiveness and saves time and money.

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Jon sits down with Brian Wilson, a retired Marine Corps Major who now heads Sagan's Knowledge and Automation group, to break down why most business owners are terrible at implementing AI and automation (and it's not for the reasons you might think).

Right off the bat, Brian gives us a reality check: most people creating content about AI and automation have never actually turned wrenches in a real business. They're content experts, not practitioners. He shares stories from live training sessions where it takes 23 minutes just to get someone to admit what their actual problem is, because everyone's been conditioned to think they need complex tech solutions instead of addressing the real issues.

They dive deep into the "duct tape and zip ties first" philosophy: why you should always try the simplest possible solution before building anything fancy. Brian tells the story of talking a nonprofit out of a $20,000 custom CRM when a $1,600/year data entry person could handle everything with a spreadsheet.

The second half gets into the psychology of why business owners get seduced by shiny new tools instead of mastering the fundamentals. Using Marine Corps doctrine and CrossFit analogies, Jon and Brian explain why the most successful people use the simplest tools with virtuoso-level execution.

They wrap up by introducing Sagan's new "skill sprints", 30-day challenges designed to build real automation habits through daily practice with a cohort, starting with company wikis in August.

Key Topics:
(03:08) Why Most AI Content Creators Have Never Actually Solved Real Problems
(11:18) When SaaS Solutions Actually Make Your Problems Worse
(16:08) The "Duct Tape and Zip ties First" Philosophy of Automation
(24:36) Why Action Produces Information (And Planning Doesn't)
(34:27) The Power of 30-Day Skill Sprints for Building Automation Habits