William Holsten’s Burnout, Heart Surgery & Reinvention: The Power of Mental Health in Business

Most entrepreneurs wait until something goes wrong before thinking about systems, customer retention, or business automation. And when those problems hit, they cost time, money, and momentum. William Holston learned this the hard way—from carnival-style side hustles that flopped to nearly losing a deal because of a wrong phone number. But instead of giving up, he turned each mistake into a lesson, eventually creating tools like the “Uh-Oh Checklist” to help entrepreneurs catch the gaps before they cost them.

In this episode, William walks us through the common business traps he sees over and over—from skipping follow-up to missing automations—and how he helps entrepreneurs fix them fast. He shares the “Uh-Oh Factor” framework, explains how to evaluate where your business is leaking money, and offers tactical advice for protecting your time, profits, and peace of mind.

Key Takeaways:

• Turning Mistakes into Momentum: William shares how early product failures with PitchBurst taught him to embrace mistakes as catalysts for redesign and reinvention.

• The “Uh-Oh” Method: His book introduces a proactive system to help entrepreneurs identify potential disasters before they happen, using tools like the “pre-mortem.”

• Mental Health & Entrepreneurship: After undergoing open-heart surgery, William emphasizes the critical importance of slowing down, setting boundaries, and protecting mental well-being.

• The Power of Oology: William explains how “Oology”—his humorous take on self-awareness—helps business owners get honest about their blind spots and biases.

• Don’t Go It Alone: He stresses the value of community, collaboration, and asking for help—especially when a simple conversation could prevent an expensive mistake.

About the Guest:

In the world of entrepreneurship, unexpected blunders can strike at any moment, leaving even the most seasoned business leaders uttering "Uh-Oh!" In his insightful new book, William Holsten draws from his own rollercoaster journey with WhirlWhims LLC to offer a candid look at the pitfalls and triumphs of launching and sustaining a business.

Holsten expertly navigates the landscape of common missteps we all encounter in personal and professional settings with a blend of humor and hard-earned wisdom. Through engaging anecdotes and relatable examples, he illustrates a variety of blunders that can lead to unintended consequences. But Holsten doesn’t stop at just identifying the pitfalls; he empowers readers with ten practical tools designed to help avoid these missteps.

"UH-OH!" is more than just a recounting of mistakes and missteps; it's a practical toolkit for resilience and strategic planning. Holsten emphasizes the importance of learning from mistakes-both his own and those of others-and provides actionable strategies to anticipate and mitigate risks. Through engaging narratives and real-world examples, readers are encouraged to embrace innovation and creative problem-solving as essential tools for overcoming obstacles.

Whether you're an entrepreneur seeking to sidestep common pitfalls or a business professional aiming to sharpen your strategic acumen, "UH-OH!" offers valuable insights into the relentless pursuit of success amidst the unpredictable nature of business.

Links:

https://williamholsten.com/

https://www.linkedin.com/in/william-holsten/

Fast Five Questions:

1. If you woke up and your business was gone, you have $500, a laptop, a place to live, and food, what would you do first? “I'd take my wife on a trip. At this stage of life, joy...