My guest for Episode #316 of the My Favorite Mistake podcast is Jim Schleckser, founder and CEO of The CEO Project.

Episode page with video, transcript, and more

Jim is a seasoned business leader, bestselling author, and trusted advisor to CEOs around the world. With experience spanning 42 countries and multiple industries, Jim has spent decades helping leaders grow their companies and think more strategically. He’s also the author of Great CEOs Are Lazy and Professional Drinking, and he’s a certified sommelier—something we get to at the end of the episode!

In our conversation, Jim shares a formative early-career mistake—being too optimistic as a leader. His enthusiasm led to overpromising revenue, under-delivering on results, and ultimately damaging his credibility to the point where he had to leave the organization. Jim reflects on how he’s since learned to balance positivity with realism, buffer commitments, and truly listen to skeptics on his team. His story is a powerful reminder that leadership isn’t just about vision—it’s also about judgment, humility, and learning from painful experiences.

We also dive into what it means to be an effective CEO, including why Jim says great CEOs are lazy. He shares how high-performing executives focus their time on removing bottlenecks, not micromanaging, and why a trusted CEO peer group can be a game-changing support system. Plus, for fellow wine lovers, we cap off the episode with a fun bonus: wine mistakes, how to order like a pro, and Jim’s best tip for getting the most out of a wine list.

• What’s your favorite mistake, and what did you learn from it?
• Can you share specific examples of how your optimism led to overcommitment or missed expectations?
• How did that mistake affect your credibility and position in the company?
• How have you learned to balance optimism with realism in leadership?
• What’s your approach to setting stretch goals versus achievable targets?
• How can unrealistic goals create dysfunction or unethical behavior in organizations?
• What’s the best way to avoid data manipulation and maintain integrity in performance reporting?
• What is The CEO Project, and how does a CEO peer group provide value to its members?
• You say “great CEOs are lazy”—what does that really mean, and how does it work in practice?
• How can CEOs identify the biggest constraint or bottleneck in their business?
• Why do some CEOs struggle to admit mistakes, and how does that affect their leadership credibility?
• How do peer groups foster psychological safety for leaders?
• What inspired you to become a certified sommelier?
• What are some common mistakes people make when ordering wine?
• What’s your best tip for confidently ordering wine at a restaurant?
• If someone only drinks Napa Cabernets, what’s a good way to branch out?
• Have you observed gender bias in how sommeliers treat guests at the table?

My guest for Episode #315 of the My Favorite Mistake podcast is Kat Halushka, a business and visibility strategist for coaches, consultants, and speakers. She’s the founder of Profitable Impact Academy, where she helps entrepreneurs grow their audience, automate marketing, and land clients through speaking and streamlined funnels.

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Kat’s favorite mistake? She followed the classic advice to “go to networking events and have coffee meetings” to get clients—so she did, hundreds of times. But after exhausting herself with back-to-back coffee chats every Friday, she realized the ROI just wasn’t there.

Kat had a breakthrough when she nervously gave a short talk at a networking event—and walked away with two new clients that day. That lightbulb moment launched her on a mission to get in front of the room instead of meeting people one-on-one. Over time, she built her credibility by hosting her own events, attracting hundreds of attendees and growing a thriving business community. This shift helped her discover that strategic speaking, not endless small talk, was the true key to visibility and client conversion.

Today, Kat teaches entrepreneurs to stop chasing every opportunity and instead focus on clarity, messaging, and scalable systems. She shares powerful lessons on why most new speakers fail to connect—and how you can avoid those pitfalls by making offers that speak to your audience’s present-day pain points. Whether you’re brand-new to business or looking to scale with less hustle, Kat’s insights on visibility, messaging, and mistake-making will help light the way forward.

• What’s your favorite mistake?
• How did those endless coffee meetings affect you and your business?
• What changed after that first speaking engagement?
• How did you start landing more speaking opportunities after that breakthrough?
• What was the origin story behind Profitable Impact Academy?
• What are some of the most common mistakes entrepreneurs make when trying to grow through speaking?
• How can business owners get clearer on what their audience really needs?
• Why is it a mistake to create too many offers or talks?
• How do you help clients identify and refine the one talk that drives results?
• What are the differences between speaking as a business vs. speaking to grow a business?
• When offered a speaking fee, how do you decide whether to accept or negotiate for something else?
• Can you explain what you mean by making an “offer from the stage”?
• How do you structure a win-win-win when working with event organizers?
• What’s one way speakers can make a compelling call-to-action without sounding salesy?
• Can you give an example of a “gift” that actually gets audience engagement?
• What’s your final advice for new entrepreneurs or aspiring speakers?

In this special bonus episode of My Favorite Mistake, host Mark Graban welcomes back Josh Cunningham, founder and CEO of Rokrbox and guest from Episode 244. Josh returns to share insights from his brand-new book, Culture Is the Key: How to Unlock Massive Profits and Freedom.

We dive into:

• How Josh built a culture-first company that’s thriving—even in a tough real estate market

• Why cutting costs doesn’t have to mean cutting people or quality

• The inspiration and process behind writing his book

• What it means to create a Five-Star Company Culture

Josh also reflects on what he’s learned since his last visit, including the power of simplification, scaling with intention, and how purpose has driven Rockerbox's explosive growth.

“Culture isn’t just a vibe—it’s the engine behind every result.” “We asked: What’s the least amount of work a person has to do to move the needle—and how can we reward them more for it?”

📕 Grab the book: Culture Is the Key is available now on Amazon and Barnes & Noble

🎧 Listen to Josh’s first episode: My Favorite Mistake #244

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