Most people wait until it’s too late to capture a loved one’s story. They assume there’ll be more time, more chances, more tomorrows. For Chance McClain, that realization came just days after filming his stepfather’s life story—he passed away five days later.

What started as a favor for a friend turned into a calling. A single interview turned into a thriving business, Heritage Films, with over 800 documentaries created across 40 states. From World War II veterans to multi-generational ranchers, Chance is preserving legacies one story at a time—and redefining what it means to pass down more than just possessions.

In this episode, Chance shares how losing his father gave birth to a company, the power of storytelling in families, and how even a CPA’s story can move generations to tears.

Key Takeaways:

• The Accidental Business: How a one-time favor became a legacy company serving families across the U.S.

• Stories That Sell (Without Selling): Why personal narratives are more powerful than any pitch—and how Chance "sells" wisdom, values, and connection to future generations.

• Systematizing Legacy: The behind-the-scenes process that allows Chance to scale highly emotional, 3-hour films while keeping each one deeply personal.

• AI + Storytelling: How Chance uses ChatGPT and Notebook LM to prep interviews, build SOPs, and keep creative energy flowing.

• Launching Farm and Ranch Films: A new brand for multigenerational agricultural families—where the land itself becomes a character.

• Why Freedom = Play: Chance’s long-term vision of choosing only the stories he wants to tell while his systems handle the rest.

About the Guest:

Chance McClain is a creative powerhouse, blending a rich background in filmmaking, radio, and theater with a passion for storytelling. As the founder of Heritage Films, Chance has created more than 800 feature- length documentaries, celebrating family stories and life legacies. His work has connected generations, preserving the essence of individuals and families through visually stunning films.

A proud Army veteran and a pioneer in narrative innovation, Chance’s career spans sports radio, Broadway musicals, and entrepreneurial filmmaking. From directing a Streamy-nominated film to writing and producing an off-Broadway musical while running a sports station, his versatility and dedication shine through.

Today, Chance leads his team at Heritage Films with a heartfelt commitment to authenticity, merging technical expertise with an artistic touch. Whether inspiring others to embrace their past or discussing the art of storytelling, he captivates audiences and helps them see the value in preserving their own legacies

Links:

https://yourheritagefilm.com/

https://www.linkedin.com/in/chancemcclain/

https://www.youtube.com/@YourHeritageFilm

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 shoot a heritage film on my iPhone. Then I'd use that money to upgrade equipment, do another, and grow from there. I’d be back in under a year."

2. What is the biggest mistake that you have made in business? "I had early success, built an Excel sheet with fantasy projections—$1M/month by Year 3. The real success felt like failure because of that unrealistic spreadsheet."

3. What is a book that you would...

Are you a hobbyist dreaming of turning your passion into real profit?

Too many creatives stay stuck, unsure how to scale their side hustle without burning out or going broke.

Stoane, founder of Wood and Stone, went from cleaning job sites to building a 7-figure woodworking business—all while staying true to his craft. In this episode, Jeff and Stoane dive deep into how you can start small, scale smart, and turn your passion into a profitable Freedom Day engine.

In this episode, he shares how he went from scraping together $5,000 and 20 hours a week... to leading a thriving business with million-dollar contracts, eight employees, and full benefits. If you've ever dreamed of turning your passion into a profitable business, Stoane's story will challenge, equip, and inspire you.

Key Takeaways:

• Start Before You're Ready: Why starting messy beats waiting for perfect

• Accounts, Not Jobs: How long-term relationships—not one-off gigs—built his 7-figure business

• Burnout Warning Signs: Stoane’s personal experience with overwork and the hidden cost of ignoring health

• Follow the Market: The difference between building what you want vs. what people are willing to pay for

• Scale Smart: Why hiring too fast can hurt you—and how to avoid expensive missteps

• Networking That Works: From lunch-and-learns to Woodcraft, Stoane shares where to find real leads (not just likes)

About the Guest:

Throughout his 20+ year career in construction, Stoane has had the opportunity to work on some magnificent projects. The majority of these projects focused on cabinetry, custom furniture and architectural features. From exotic wood desks for C-level Executives to Trade show booths featured at the Paris Air Show to many Homes, Offices, Hotels and Restaurants throughout the USA.

General Contracting: He has worked his way up from the production line in a cabinet shop, into custom furniture and fixtures, estimating, project management, shop management and now ownership. Through the years there have been a lot of wins and a lot of lessons!

Helping the Next Generation: Stoane has made it his Mission to help others skip avoidable hurdles. He consults with contractors on their business and teaches classes, across multiple states, around woodworking, carpentry and making money in the trades.narratives and real-world examples, readers are encouraged to embrace innovation and creative problem-solving as essential tools for overcoming obstacles.

Links:

https://woodandstoane.com/

https://www.facebook.com/woodandstoane/

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? "Get a job building for someone else. Then a second gig at Woodcraft or Rockler. Monetize every minute until I can get a bankroll to go back out."

2. What is the biggest mistake that you have made in business? "Hiring for resume over character. And real burnout—I hit a wall that affected my health."

3. What is a book that you would recommend? "Extreme Ownership by Jocko Willink and Never Split the Difference by Chris Voss."

4. What is a tool that you use every day that you would recommend? "A bookkeeper—get one sooner than you think. And a Festool track saw. Game changer."

5. What is your definition of freedom? "Making decisions that are best for my family and having the resources to make them happen. I found I love what I do—and

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...