The $10,000 Mistake Checklist: How to Prevent Business Blunders Before They Cost You

What if you could predict and prevent the costly mistakes that sink most businesses before they happen? In this episode, I sit down with William Holsten, a Business Mistake Prevention Specialist who's on a mission to help entrepreneurs avoid the expensive blunders that derail success.

Bill shares his own entrepreneurial journey – including the painful "uh-oh moment" when multiple customers called to complain about his invention after launch. He'd spent nearly $100,000 producing 100 units of a carnival game without proper testing, and the pieces were literally falling apart. The mistake nearly destroyed his business, but the lessons he learned transformed how he thinks about entrepreneurship.

Now retired from a established career at Bayer (where he led innovation for brands like Bayer Aspirin and Alka-Seltzer), Bill is conducting a entrepreneur study on business mistakes and has discovered something fascinating: 80% of entrepreneurs made one or more business-impacting mistakes in the past year, yet almost everyone rates their risk of making mistakes in the next 30 days as low.

In this episode, you'll discover:

- How building funnels based on your own assumptions (not what customers actually think) is a costly mistake

- The two specific tools that could have saved Bill $100,000 (and how you can use them)

- Why "test and learn" isn't optional – it's essential for survival

- How mapping your customer's actual experience reveals hidden problems

- The power of asking "How might we..." instead of "What's wrong with this?"

- Why entrepreneurs silo themselves and miss obvious solutions

- The dangerous pattern of jumping into business without a solid plan

- Creative problem-solving techniques borrowed from Picasso and Dr. Seuss

Key frameworks revealed:

The "Look in the Mirror" exercise for identifying your mistake patterns

The $10,000 Mistake Checklist (free download on Bill's website)

How to think through problems using different lenses

When to ask for help versus trying to solve everything alone

Bill doesn't just tell you what to do – he helps you develop the creative problem-solving skills to handle whatever challenges come your way. Because fixing mistakes is expensive, but preventing them is priceless.

About William (Bill) Holsten:

William Holsten is a Business Mistake Prevention Specialist, author of "Uh-Oh: Entrepreneurial Business Moments," and volunteer mentor with SCORE. With a 30-year career at Bayer leading brand management and innovation for major brands like Bayer Aspirin and Alka-Seltzer, Bill became an expert at generating new business ideas and solving complex problems using creative tools and workshops.

Bill and his wife Janet launched Whirlwinds LLC, where they developed and patented five carnival games – learning expensive lessons about entrepreneurship the hard way. Now he's dedicated to helping other entrepreneurs avoid the costly mistakes he made. Bill is a graduate of the Creative Education Foundation's Creative Problem Solving Institute and is currently conducting a comprehensive study on entrepreneurial mistakes to help business owners identify their risk factors and prevent blunders before they happen.

Connect with Bill: WilliamHolsten.com Free resource: Download the $10,000 Mistake Checklist LINKEDIN: https://www.linkedin.com/in/william-holsten/

Biz in a Box CRM is the ultimate all-in-one solution designed to simplify and scale your business. Imagine managing every aspect of your operations — from smart contact segmentation and automated follow-ups to call and text functionality, calendar booking, funnels, websites, and even social media scheduling — all from one intuitive platform. No more juggling multiple tools or paying for endless subscriptions. With built-in AI employee support, Biz in a Box CRM doesn’t just organize your business, it actively helps you run it. It’s like having a full-time team behind the scenes, so you can focus on growth, impact, and freedom.

Book your demo: https://bizinaboxsolutions.com/

In just 15–20 minutes, I can help you uncover the hidden inefficiencies that are costing you both time and money in your business. Most owners don’t realize how much energy is wasted on repetitive tasks, gaps in processes, and systems that don’t actually support growth. During our call, I’ll listen closely to how your business is currently running, pinpoint one or two areas where you may be sabotaging your own scalability, and show you a clear next step to reclaim control. Whether you decide to work with me further or not, you’ll leave with immediate clarity on what’s holding your business back — and the confidence of knowing exactly where to focus to create more freedom and profit.

Book here - https://crm.bizinaboxsolutions.com/widget/bookings/15-minute-consult-ls

Mentioned in this episode:

The Clockwork Method

Is your business the baby that never grows up? It keeps you up at night, interrupts date night, and forget taking a vacation because you can't ever find the right sitter. Good news - our signature Clockwork Method program turns your business into the independent, thriving operation it was meant to be.We help you build the processes that empower the people to scale the profitability without you micromanaging every detail. The Clockwork Method isn't just another coaching program that leaves you with a heap of to-do's to add to your plate. In this program we build the systems with you, handling the big tech heavy lifting that just slows you down. Ultimately the clockwork method is here to help you transform your business from needy, dependent operations into mature businesses that runs itself. Discover more today at https://theclockworkmethod.com