How to prevent business failure before they cost you your business. In this blog, we dive into practical strategies for entrepreneurs, pulling wisdom from the real-life journey of carnival game inventor William Holsten. You’ll learn how to reflect on your own patterns, empathize with customers, plan ahead, and use others’ failures to build your success story. Whether you’re new to entrepreneurship or looking to stabilize your current venture, this guide will help you stay ahead of trouble and grow smarter.
About This Huddle’s Special Guest
William Holsten is a retired corporate marketer and innovation expert turned small business mentor and inventor. With a career spanning more than 30 years, William led global brand teams for a major multinational, guiding product development and innovation workshops around the world.
His entrepreneurial journey began unexpectedly in 1999 when he invented Pitch Burst, a water-balloon game alternative to the traditional dunk tank, for a charity event. The product’s success sparked a side business that eventually grew into a full venture, including patents and new game concepts. But like many entrepreneurs, William learned the hard way that product durability, customer feedback, and business planning are non-negotiable for sustainable growth.
Today, William mentors entrepreneurs through SCORE and shares his experiences in his book, “Uh-Oh: Avoid Unintentional Blunders That Derail Entrepreneurial Success and Goof-Proof Your Business.” His writing focuses on helping small business owners prevent business failure mistakes and adopt smarter, more strategic approaches.
Through his talks, writing, and Uh-Oh-ology newsletter, William helps entrepreneurs reflect, plan, and move forward with greater confidence—learning from his journey so they don’t have to repeat it.
The Real Cost of a Mistake
Every small business owner hits a few bumps. But sometimes, a small misstep can snowball into a costly disaster. In this article, we unpack practical lessons from William Holsten, a retired corporate marketer turned carnival game inventor, who turned his uh-oh moments into business wisdom. The truth is, learning how to prevent business failure is essential for survival. Mistakes are inevitable, but how you respond and learn from them can determine whether you thrive or close your doors. It’s not about eliminating all errors—it’s about creating systems and habits that minimize their impact. Think of it as business insurance through better planning. A moment of reflection, an early warning sign, or a well-placed safeguard can turn a potential catastrophe into a manageable hiccup. Understanding the value of every decision and anticipating its consequences can be your best defense against costly errors.
Why “Avoid Small Business Mistakes” Matters
When running a business, you juggle a thousand things at once. Missing one—like customer expectations, product durability, or insurance renewals—can be enough to put you out of business. That’s why it’s critical to understand how to avoid small business mistakes before they derail your momentum. Many entrepreneurs launch with great ideas but fail to lay the groundwork for sustainable growth. Without systems in place to catch small oversights, one misstep can snowball. Whether it’s an underperforming product, a missed contract renewal, or poor communication, these “uh-oh” moments accumulate and damage credibility. Avoiding small business mistakes doesn’t mean never trying something new—it means testing smart, planning ahead, and being honest with yourself. Building resilience into your process and being willing to learn from others are the keys to long-term success.
Real-World Example: The Pitch Burst Invention
William Holsten’s entrepreneurial journey began with a problem: a drought meant no dunk tanks for a charity event. So, he and his wife invented Pitch Burst, a water balloon alternative. The invention was a hit—but their first version lacked durability. They sold 60 units, only to watch them break down. The lesson? Test for real-world use. What followed was a pivot to stronger materials and a long-term business success. What’s striking is not just the creativity behind Pitch Burst, but the hard-earned realization that early wins can lead to costly regrets if products aren’t built to last. Holsten’s story is a reminder that MVPs (Minimum Viable Products) are only step one. Entrepreneurs need to “kick the snot out of it,” stress-testing ideas before going to market. Otherwise, the cost of replacements, refunds, and damaged reputation can erode everything you’ve built. That one moment of skipping durability testing led to a major pivot—a lesson every small business owner can learn from.
4 Core Areas to Goof-Proof Your Business
1. Understand Yourself
To avoid small business mistakes, start with you. Reflect on your own tendencies: Are you a perfectionist who delays launches? Or a risk-taker who skips the fine print? Take five minutes to list your biggest mistakes over the past year. What caused them? Stress? Fatigue? Rushed decisions? By understanding your own patterns, you can put safeguards in place—like checklists, co-reviewers, or just knowing when to stop working. One powerful method is the “Look in the Mirror” tool Holsten describes: jot down the blunders you’ve made and cross-reference them with common triggers. Knowing your weaknesses isn’t a liability—it’s a leadership strength. Self-awareness in business is a superpower. It helps you make smarter decisions and set up processes that protect your vision, even when you’re having an off day.
2. Understand Your Customers
Knowing your audience is more than demographics. It’s about empathy—how do your customers feel when using your product or service? Many entrepreneurs assume too much and end up solving the wrong problems. Start by interviewing 5–10 customers. Listen deeply. What are their frustrations, joys, and workarounds? Map their journey: what do they think, feel, do, and say? Then compare it to your assumptions. Any gap is a risk to your business. Adjust your product, messaging, or instructions accordingly. Design thinking teaches that customer experience isn’t a “nice to have”—it’s your blueprint for success. When you understand your customers’ true behavior and expectations, you gain insights that no analytics dashboard alone can reveal. And the earlier you apply those insights, the fewer costly revisions you’ll face down the road.
3. Plan for the Future
Forward thinking is the best antidote to reactive scrambling. One standout technique from Holsten’s toolkit is the “pre-mortem”—a reverse-engineering exercise where you imagine your business failing two years from now. Why did it fail? What went wrong? Brainstorm every possible reason, from a big-box competitor moving in to customer confusion about your offer. Once you’ve listed them, rank by likelihood and impact. Then take preemptive action: adjust pricing, clarify messaging, or fortify your supply chain. The beauty of this exercise is that it transforms anxiety into action. It allows you to visualize setbacks while you still have the power to prevent them. Rather than reacting to problems, you become a proactive strategist who anticipates risks and builds safeguards in real time.
4. Learn from Others’ Mistakes
Warren Buffett once said, “It’s good to learn from your mistakes. It’s better to learn from other people’s mistakes.” That’s the heart of what Holsten calls “Uh-Oh-ology.” From Steve Harvey’s Miss Universe mix-up to Crystal Pepsi’s failed rebrand, the world is full of costly lessons—if you’re willing to look. When you observe what went wrong and apply it to your context, you sidestep the emotional and financial toll. As a small business owner, time is precious. Instead of paying for your own lessons, study others’ failures. Reflect on how a forgotten insurance renewal, bad assumption about durability, or misaligned customer experience led to collapse. Then, tweak your own process to avoid similar traps. The goal isn’t to avoid risk altogether, but to be smarter about it.
Weekly Action Plan
- Week 1: Self-Reflection with the “Look in the Mirror” Tool
Set aside one hour in a quiet place and make a list of the top five business mistakes you’ve made over the past year. Identify patterns or triggers—were you rushing, exhausted, or under pressure? Use this list to identify three changes you can implement immediately, like delegating certain decisions or using a pre-launch checklist. - Week 2: Customer Interviews & Journey Mapping
Reach out to 3–5 loyal or recent customers. Ask them about their full experience—from discovering your business to post-purchase feedback. Take notes on what they loved, where they struggled, and what they misunderstood. Map these insights visually to uncover blind spots, then use this to improve messaging, support, and product design. - Week 3: Conduct a Pre-Mortem Workshop
Gather your team for a half-day session. Pretend your business failed two years in the future. List every reason why—no matter how wild. Rank them by likelihood and impact. Choose three high-priority risks and assign action items to mitigate them now. Document the session and revisit it quarterly. - Week 4: Study a Famous Business Blunder & Apply It
Pick one famous case (like New Coke or a local competitor’s failed launch). Analyze what went wrong and why. Write a short paragraph on how your business could face a similar risk—and what you’ll do to avoid it. Share it with your team or post as a blog to turn the lesson into content.
Final Thoughts
William’s story is a reminder that even great ideas can flop without planning, testing, and honest reflection. To avoid small business mistakes, adopt a mindset of continuous learning and calculated risk-taking. Whether you’re inventing carnival games or launching your first local service, success comes from smart strategy and being ready to adapt. It’s not enough to work hard—you have to work smart. And that means investing time upfront to avoid cleanup later. Mistakes will happen, but armed with the right tools, they don’t have to define your business.
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Transcript
- 0:00 | Intro: Meet William Holsten
- 0:21 | From Corporate Innovator to Inventor
- 1:03 | The Birth of PitchBurst
- 2:18 | Going from Side Hustle to Full Business
- 3:34 | First Big Failure: The Uhoh Moment
- 4:51 | Reinventing a Product After Failure
- 6:13 | Why Entrepreneurs Make Costly Mistakes
- 7:30 | Famous Blunders and Business Lessons
- 9:00 | The 10 Tools to Goofproof Your Business
- 10:00 | Tool 1: Look in the Mirror
- 11:44 | Tool 2: Understand Your Customer
- 12:44 | Tool 3: Premortem Planning
- 14:32 | Tool 4: Learn from Other People’s Mistakes
- 16:04 | Entrepreneur Optimism and Risk
- 18:26 | Why Most Business Failures Are Preventable
- 20:54 | Small Errors That Kill Businesses
- 22:00 | Testing Prototypes Like a Pro
- 24:00 | The Power of “Test and Learn”
- 26:09 | Selling the Business After Health Scare
- 27:22 | Lessons from Water Wars and Durability Testing
- 29:08 | Why Perfection is the Enemy of Progress
- 30:30 | When to Pivot, Quit, or Persist
- 33:04 | Avoiding the ‘Ignore It’ Mentality
- 34:06 | How to Recognize When It’s Time to Quit
- 36:09 | Understanding Your Entrepreneurial Blind Spots
- 37:10 | Free Tool: “Why the F Did I Do That?” Self-Assessment
- 38:44 | Who the Book is For: Entrepreneurs & Small Biz Owners
- 40:06 | Get Help: Mentors, Experts & Naive Observers
- 42:21 | Real-World Testing: Feedback from Strangers
- 44:17 | Business Expo Elevator Pitch Strategy
- 47:01 | Where to Find William Holsten Online
- 47:55 | Final Thanks and Wrap-Up
0:00 | Intro: Meet William Holsten
Dean and Rob kick off the episode by introducing William Holsten, who shares the story of how a career in corporate marketing transitioned into a creative journey of invention. He talks about his work with global brands and how he later found joy and purpose in creating carnival games. The introduction highlights the unexpected twist from boardroom meetings to backyard events, setting the tone for a blend of inspiration, problem-solving, and small business storytelling. How to prevent business failure starts by hearing from someone who’s lived through the ups and downs.
0:21 | From Corporate Innovator to Inventor
William Holsten reflects on his corporate background and explains how his expertise in innovation directly influenced his ability to create products that people love. As he speaks with Dean and Rob, he discusses his mindset shift from innovating for global corporations to developing his own ideas. He emphasizes the value of repurposing professional skills into personal ventures, making this a key moment for professionals considering entrepreneurship. The conversation reveals how to prevent business failure by applying learned strategies from larger organizations.
1:03 | The Birth of PitchBurst
William Holsten recounts how a drought in 1999 disrupted plans for a Make-A-Wish carnival, forcing him to invent a fun water game alternative to the traditional dunk tank. From this challenge came PitchBurst—a new type of water balloon game. Using simple materials from Home Depot, he and his wife created the prototype at their kitchen table. The overwhelming reaction at the charity event proved the concept, demonstrating how limitations can unlock creative innovation. A small pivot helped prevent business failure before it began.
2:18 | Going from Side Hustle to Full Business
Interest in PitchBurst skyrocketed after the event, and William Holsten decided to transform his side project into a legitimate business. With an SBA loan and early sales, the venture gained traction. However, the first manufactured units proved too fragile for repeated rental use, leading to product returns and financial strain. This chapter illustrates the high-stakes learning curve entrepreneurs face when scaling a product from passion to professional. How to prevent business failure means learning from misfires during your growth stages.
3:34 | First Big Failure: The Uhoh Moment
In this pivotal moment, William Holsten describes the crushing realization that his product wasn’t holding up in the field. Rental companies were demanding replacements and refunds, quickly draining all his capital. He calls it the “uh-oh moment”—a point of no return where business reality collides with entrepreneurial optimism. This segment offers a raw look at vulnerability and the importance of anticipating operational stress points. Recognizing such moments early is crucial if you want to know how to prevent business failure.
4:51 | Reinventing a Product After Failure
After nearly closing shop, William Holsten partners with an engineer to redesign Pitch Burst using steel, ensuring durability for commercial use. He details how the shift from makeshift materials to robust engineering gave the product a new life. The decision to invest in expert collaboration marks a turning point in his journey, reinforcing the lesson that seeking help and improving upon failure is not weakness, but strategic resilience. This story is a vivid example of how to prevent business failure through continuous improvement.
6:13 | Why Entrepreneurs Make Costly Mistakes
As the conversation deepens, he explains the psychology behind common entrepreneurial mistakes. Drawing from personal experience and broader business insights, he outlines how stress, overconfidence, and assumptions often cloud judgment. He and the hosts explore how these errors are usually not from lack of effort, but from a lack of self-awareness and preparation. His message is clear: understanding your internal drivers is a foundational step in how to prevent business failure, especially in high-stakes decisions.
7:30 | Famous Blunders and Business Lessons
William and the hosts turn to well-known mistakes from big names like Steve Harvey and major brands like Coca-Cola and Ford. By analyzing the missteps of high-profile figures and corporations, they emphasize that no business is immune to blunders. William shares the concept of “uh-oh-ology,” encouraging entrepreneurs to study others’ failures so they can avoid making the same ones. This segment is both entertaining and educational, packed with examples that bring humor and gravity to the topic of business misjudgment.
9:00 | The 10 Tools to Goofproof Your Business
William introduces his framework for preventing small business disasters: ten tools designed to help entrepreneurs foresee and neutralize potential mistakes. Each tool is rooted in real experience—his own blunders and corporate lessons—and offers a practical method for assessing risk, understanding behaviors, and creating safer systems. He explains that goofproofing isn’t about perfection—it’s about preparation. These tools are built for business owners who want to be proactive instead of reactive.
10:00 | Tool 1: Look in the Mirror
The first tool challenges entrepreneurs to face their own patterns. William explains how creating a list of personal mistakes and matching them to common causes—like fatigue or assumptions—reveals a blueprint for future errors. Through this exercise, business owners can identify risk patterns in their own behavior. Dean and Rob discuss how such self-reflection, while uncomfortable, is one of the most empowering steps in preventing repeat mistakes. It’s the foundation for how to prevent business failure from within.
11:44 | Tool 2: Understand Your Customer
William shares how many entrepreneurs assume their customers will use their product a certain way—until they don’t. This tool calls for mapping the customer journey by interviewing and observing actual users. It’s about empathy over assumption. By understanding what the customer feels, does, and needs, business owners can better design their products, messaging, and delivery. This tool reminds listeners that guessing leads to gaps, and gaps lead to failure. Real insight is the only bridge to long-term success.
12:44 | Tool 3: Premortem Planning
In this imaginative yet strategic exercise, William invites teams to pretend it’s two years later and their business has failed. Why did it happen? The “premortem” allows entrepreneurs to brainstorm potential disasters before they occur and then prioritize which risks are most likely and most damaging. From there, they can design preventative strategies. Dean and Rob note how this future-focused approach helps entrepreneurs act today to avoid tomorrow’s downfalls. It’s a must-have method on how to prevent business failure.
14:32 | Tool 4: Learn from Other People’s Mistakes
William reinforces the value of observing others’ failures. He introduces the concept of “Uh-Oh-ology,” encouraging business owners to become students of error. From major brand failures to small-scale stumbles, he emphasizes the importance of analyzing the context, understanding what went wrong, and applying those lessons to one’s own business. By learning vicariously, entrepreneurs can sidestep disasters they haven’t yet faced themselves. Dean and Rob appreciate how this tool turns failure into a universal teacher.
16:04 | Entrepreneur Optimism and Risk
William explains how entrepreneurial optimism, while vital for innovation, often blinds business owners to realistic risks. He discusses how confidence can lead to oversight and how unchecked positivity might prevent one from seeing early warning signs. Rob and Dean reflect on their experiences with business owners who waited too long to pivot. William suggests balancing optimism with objectivity to avoid preventable collapse. The lesson: hope fuels growth, but awareness prevents loss.
18:26 | Why Most Business Failures Are Preventable
The hosts and William agree—most failures don’t come from bad luck but from poor preparation. William shares how early warning signs were ignored in his own journey and emphasizes the importance of acknowledging problems before they escalate. Many businesses collapse not from one big event but from accumulating small errors that were never addressed. This segment reinforces that a combination of planning, observation, and self-checks can save most ventures from failure before it’s too late.
20:54 | Small Errors That Kill Businesses
In this chapter, the focus shifts to the seemingly minor mistakes that, when left unchecked, can end a business. William gives examples such as forgetting to renew insurance or failing to lock up a storefront—small slips with massive consequences. These “uh-ohs” are preventable but often overlooked in the hustle of entrepreneurship. The takeaway: success isn’t just about bold moves but about avoiding the silent killers. A solid checklist and better habits are essential tools in how to prevent business failure.
22:00 | Testing Prototypes Like a Pro
William walks through how he tested a new game by inviting kids to play it in a hotel pool for hours. The results showed flaws in the pump system, which later became a real-world problem. His mistake? Dismissing the warning signs. Dean and Rob explore how small businesses must take testing seriously, even for basic concepts. By embracing failure during testing—not after launch—entrepreneurs can save money, time, and reputation. It’s a call to take your own trials seriously, no matter how informal they feel.
24:00 | The Power of “Test and Learn”
William introduces the corporate-tested strategy of “test and learn.” Instead of launching a product all at once, test small pieces, observe real-world reactions, and only then scale. It’s a risk-managed, data-driven approach that big companies use but small businesses often skip. He and the hosts reflect on how duct tape and feedback can be more powerful than expensive launches. The method proves you don’t need perfection to start—you just need a plan to test, listen, and adapt. It’s how to prevent business failure on a budget.
26:09 | Selling the Business After Health Scare
William shares a personal turning point: a health scare that included a surprise diagnosis requiring open-heart surgery. Faced with the reality that he could no longer manage both his corporate job and his carnival game business, he began the process of selling. This segment is a sobering reminder that unforeseen personal events can impact business decisions. His experience teaches entrepreneurs to plan exit strategies early and to be honest about capacity and health as critical components in long-term business success.
27:22 | Lessons from Water Wars and Durability Testing
After selling to Water Wars, William witnesses how the new owners stress-tested the products by offering them for free at top-tier water parks. This allowed for brutal but informative durability testing before official launch. He praises their “kick the snot out of it” approach, contrasting it with his own earlier mistake of skipping thorough field testing. The takeaway is clear: don’t just test lightly—test to fail. Learning how to prevent business failure often begins by seeing where and how your product breaks down.
29:08 | Why Perfection is the Enemy of Progress
In this conversation, William and the hosts explore the trap of perfectionism. Too many entrepreneurs wait until everything is flawless before launching, but in doing so, they often miss critical feedback or market timing. William shares how some of his best product insights came not from finished products but from early rough versions. The lesson? Don’t let perfect get in the way of progress. Iteration beats stagnation every time, especially for small business owners working with limited time and budgets.
30:30 | When to Pivot, Quit, or Persist
Not every product or idea works out. William outlines the five choices every entrepreneur faces after a setback: accept, fix, pivot, quit, or ignore. He explains why ignoring is the most dangerous option and why quitting is sometimes the wisest. The conversation emphasizes objective reflection over emotional decisions. Dean and Rob echo the sentiment that knowing when to walk away is a sign of maturity, not failure. This chapter gives clear criteria to evaluate next steps when facing uncertainty.
33:04 | Avoiding the ‘Ignore It’ Mentality
The discussion dives deeper into why ignoring problems is one of the most destructive habits in business. William warns that unaddressed issues don’t disappear—they grow. He shares how unchecked optimism or fear of confrontation leads entrepreneurs to overlook glaring red flags. The solution lies in awareness, action, and accountability. Dean and Rob stress the importance of addressing even the uncomfortable issues head-on. It’s a reminder that the cost of avoidance can be much greater than the pain of confrontation.
34:06 | How to Recognize When It’s Time to Quit
William introduces the idea of working with a “quitting coach”—a method to objectively assess whether a business is worth continuing. Entrepreneurs define performance benchmarks and revisit them later. If the goals aren’t met, it’s a sign to consider exiting. Dean and Rob discuss how this approach combats the delusion of false hope. The chapter challenges listeners to trade pride for practicality, giving them a toolset to evaluate whether their persistence is wise or wasteful. Sometimes quitting is the smartest play.
36:09 | Understanding Your Entrepreneurial Blind Spots
This segment focuses on how self-awareness is key to avoiding mistakes. William revisits earlier themes and stresses how blind spots—whether emotional, operational, or relational—often go unnoticed until it’s too late. Through his examples, he explains how honest reflection and feedback loops are essential to growth. Rob and Dean highlight how easy it is to fall into repetitive mistakes when self-analysis is missing. It’s a call for business owners to routinely “audit” their actions and assumptions.
37:10 | Free Tool: “Why the F Did I Do That?” Self-Assessment
William introduces a downloadable tool from his website designed to help entrepreneurs identify patterns behind their worst decisions. It’s a no-shame, solo exercise that encourages people to list blunders, link them to causes, and find patterns. The tool helps shift from guilt to growth. The hosts highlight how valuable it is to have a structured way to evaluate errors. This freebie provides a practical step toward personal improvement and is a core part of how to prevent business failure through self-awareness.
38:44 | Who the Book is For: Entrepreneurs & Small Biz Owners
William outlines his book’s audience: solopreneurs, inventors, and small businesses with under 20 employees. He shares how his own loneliness as a side-hustle entrepreneur inspired him to write a guide that felt like mentorship in a book. The conversation reminds listeners that big business tools can be adapted to small business needs. Dean and Rob appreciate how the content is approachable yet powerful. This chapter serves as a call to action for anyone who feels they’re figuring it out alone.
40:06 | Get Help: Mentors, Experts & Naive Observers
Here, William breaks down three powerful forms of help: expert advice, mentorship, and feedback from naive observers. He discusses how each offers a unique perspective and how combining them creates a holistic view of your business. He praises SCORE, a free mentoring network, and shares how talking to someone who knows nothing about your business can spark powerful insights. The trio encourages entrepreneurs to seek help proactively and regularly. Collaboration, they emphasize, is a core strategy in avoiding failure.
42:21 | Real-World Testing: Feedback from Strangers
William recalls exercises from Stanford’s D School and his experiences with feedback from strangers. He emphasizes the power of real-time, face-to-face feedback for truly understanding customer behavior. Whether on the streets of San Francisco or in a pool with test users, he argues that raw, unfiltered reactions can guide critical business adjustments. Dean and Rob reflect on how digital tools today can simulate this process. The lesson: get outside your bubble if you want to grow smart and resilient.
44:17 | Business Expo Elevator Pitch Strategy
William shares a unique benefit from attending small business expos—speed networking that forces you to perfect your elevator pitch. He explains how repeating his pitch 40 times helped him refine the core message of his book. Rob and Dean recognize how rare it is for entrepreneurs to stress-test their messaging in real conversations. This chapter is a nudge for entrepreneurs to leave their comfort zones and practice presenting with real stakes and real feedback. Messaging matters more than most realize.
47:01 | Where to Find William Holsten Online
William reminds listeners where they can find him and download the free self-assessment tool. His website, williamholsten.com, is home to the “Why the F Did I Do That?” PDF, book details, and upcoming workshops. Dean and Rob emphasize that these tools are free and accessible, reinforcing the value of starting your self-awareness journey now. This chapter acts as a CTA for deeper learning and ongoing support from a seasoned expert who has been through the entrepreneurial trenches himself.
47:55 | Final Thanks and Wrap-Up
The episode closes with warm appreciation for William’s wisdom and humor. Rob and Dean reflect on the practical value shared throughout the conversation and encourage listeners to implement at least one of the tools discussed. William thanks the hosts and listeners, reminding them that preventing business failure isn’t about being perfect—it’s about being prepared. With the right tools, the right mindset, and the willingness to learn, any entrepreneur can build a business that survives—and thrives.
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About This Huddle’s Special Guest
