Most business owners are too busy working IN their business to ever work ON it. After 30 years running Frieda's Specialty Produce, Karen Caplan knows exactly what that costs. She now coaches CEOs and leaders of companies from $10M to $200M in revenue. In this episode, Karen breaks down the three patterns keeping business owners stuck, why really wanting a shift is non-negotiable, and the four coaching questions that redefine the annual performance review forever.

About the Guest

Karen Caplan spent 30 years as CEO of Frieda's Specialty Produce, a family business whose story, including how kiwi fruit and over 200 exotic produce items made their way to American tables, is the subject of the documentary Fear No Fruit. Since selling the company, she has founded an executive coaching and consulting practice, helping CEOs and company leaders navigate the challenges of scaling. For over 15 years, she has also been sharing her thinking on business and leadership through her blog "What's on Karen's Plate".

Episode Highlight

"You have to really want it. Whether it's making a to-do list, a checklist, or deadlines for what needs to get done. You have to really want it and have the discipline to stay focused on whatever the goal is."

Actionable Insights

• Working in your business is the number one growth killer: Karen identifies the single biggest impediment to growth as owners staying buried in day-to-day operations instead of carving out time for vision, strategy, and planning. An outside perspective cuts through that blind spot fast. Most CEOs don't have someone holding them accountable unless they're part of a public company or have investors. That gap is where growth dies. [01:59]
• The pain has to get real before change happens: Karen's own wake-up moment came when her CPA told her she was 'basically spending her inheritance' to keep the business afloat. That shock was the catalyst. Comfort is a trap, and waiting for pain to peak is not a strategy. Having someone on the outside hold up the mirror is. [06:53]
• Replace annual reviews with four coaching questions: What's working well right now? Where are you feeling stuck or frustrated? What support do you need from me? What are you learning? Karen's framework transforms managers from judges to coaches. Consistency and genuine interest in the answers are what build team performance, and it has to happen biweekly, not annually. [16:15]

Ready to apply these insights to your own business? Download the free Action Kit

More About Karen Caplan

Connect with Karen on LinkedIn.

Check Out Karen Caplan

More About Rob Levin & WorkBetterNow

Like this show? Click on over and subscribe to our YouTube channel!
Follow Rob Levin on Substack.
Out now! The New Talent Playbook: The Ultimate Guide to Building Your Dream Team 📕 Available on Amazon or visit thenewtalentplaybook.com and get the free scorecard.

Most business owners face a paralyzing choice: leap into AI or wait until it's proven. Rob Levin cuts through the false binary. The cost of waiting isn't just competitive lag, it's cultural stagnation and missed efficiency gains happening right now. In this solo episode, he walks you through a practical, risk-managed framework that separates owners who'll thrive from those who'll get crushed: starting with secure infrastructure, building something yourself to demystify AI's power, then scaling adoption across your team with show-and-tell sessions and hands-on experimentation. This is about moving before your competitors do, and doing it confidently.

Episode Highlight
"The owners that are gonna come out ahead in this decade with their businesses aren't the ones with the biggest AI budget. They're gonna be the ones that started experimenting now, if they haven't started already, and hopefully got a jump over their competitors."

Actionable Insights

1. Set Up Secure Infrastructure First, Don't Skip This: Before you touch AI, talk to your IT person or hire a consultant to lock down your LLM setup, ensure data isn't being shared or used for learning, and establish a clear AI usage policy. This foundation removes fear, letting your team move confidently. [02:31]
2. Build Something Yourself to Unlock What's Possible: Don't stay in thought-partner mode. Create a custom GPT or AI agent for a recurring task you handle, takes only a couple hours. The point isn't shipping it; it's experiencing firsthand how easy AI is to use and feeling what it can do. This personal breakthrough shifts your mindset from skeptical to strategic. [05:06]
3. Reframe AI Adoption as a Job-Evolution Question, Not a Job-Loss Threat: Be transparent: companies that don't embrace AI will get crushed by those who do. But the message isn't "we're replacing you", it's "your job is changing." People using AI will outcompete people who don't. Offer training, free courses, subscriptions, and time. [10:03]

Ready to apply these insights to your own business? Download the free Action Kit

More Resources

• Inside WBN's AI Transformation

Other Episodes You Might Enjoy

• Why Waiting on AI Is Riskier Than You Think | Alan Pentz
• How WBN Is Becoming an AI-First Company

More About Rob Levin & WorkBetterNow

Like this show? Click on over and subscribe to our YouTube channel!
Follow Rob Levin on Substack.
Out now! The New Talent Playbook: The Ultimate Guide to Building Your Dream Team 📕 Available on Amazon or visit thenewtalentplaybook.com and get the free scorecard.

What separates leaders who scale from those who hit a ceiling? Damon Gersh, founder and former CEO of Maxsens Restorations, has navigated both, building a team that stayed calm and effective during 9/11 and Superstorm Sandy, then evolving from operator to strategist. In this episode, he breaks down the counterintuitive moves that unlock growth: delegating authority before you need it, maintaining non-negotiable standards that attract top talent, and fundamentally shifting from working in your business to working on it.

About the Guest

Damon Gersh is an entrepreneur best known as the founder and former CEO of Maxsens Restorations, New York's premier property damage restoration firm, which earned recognition for its leadership during 9/11 and Superstorm Sandy. A recipient of the Ernst & Young Entrepreneur of the Year Award, he has co-founded national business organizations including Restoration Affiliates and Gathering of Titans. Now mentoring and investing in entrepreneurs, real estate, and creative ventures, Gersh continues his lifelong focus on leadership, collaboration, and impact.

Episode Highlight

"A lot of times in life you look back in hindsight, and all the things that you did just moving forward make sense in the rear-view mirror"

Actionable Insights

1. Build Your Leadership Team Before Crisis Hits: The preparation work you do in calm times determines your capacity in chaos. By educating his team, delegating authority, and giving leaders room to make mistakes, he built what he calls "decision-making muscles." [02:29]
2. The Leader Sets the Tone, Even When Scared: On crisis days, people are watching you. Gersh was internally uncertain and scared on 9/11, but he knew his job was to project confidence, calm, and control. That psychological anchor, your visible composure, lets your team move into action mode rather than panic mode. [03:41]
3. High Standards Attract High Performers, Culture Self-Selects: Gersh was raised in the old-school service business ethos: all you have is your reputation and good name. He maintained rigorous standards of professionalism and quality, which he embodied as a leader. The result? Top performers wanted to work there. [08:02]

Ready to apply these insights to your own business? Download the free Action Kit

More About Damon Gersh

Connect with Damon on LinkedIn.

More Resources

Grab your copy of The E-Myth by Michael Gerber

More About Rob Levin & WorkBetterNow

Like this show? Click on over and subscribe to our YouTube channel!
Follow Rob Levin on Substack.
Out now! The New Talent Playbook: The Ultimate Guide to Building Your Dream Team 📕 Available on Amazon or visit thenewtalentplaybook.com and get the free scorecard.