#64 Productive Discomfort: The Price Every Great Leader Must Be Willing to Pay with Boaz Gilad author of The Zenith Code

#64 Productive Discomfort: The Price Every Great Leader Must Be Willing to Pay with Boaz Gilad author of The Zenith Code

Have you ever noticed that some of the most successful people you know have it all figured out in one area of life... and are quietly falling apart in another? The CEO who can close a nine-figure deal but can't stick to a diet for two weeks. The entrepreneur who built an empire from nothing but hasn't had a real conversation with his own kid in months. We've all seen it. Maybe you've lived it. This week, I sat down with Boaz Gilad [https://www.zenithclubhouse.com/] — former real estate CEO turned performance coach and author of The Zenith Code — to talk about why this happens, and what it actually takes to break the pattern. Boaz's story is one of the most unconventional paths to leadership I've featured on this show. He grew up in Jerusalem, served as a paratrooper in the Israeli army, then moved to New York at 22 to chase a completely different dream — acting. He trained at the Stella Adler Conservatory, studied Philosophy at Hunter College, and waited tables to make ends meet. A real estate side hustle turned into a 20-year career that took him to CEO of a public company and made him a driving force in Brooklyn's real estate resurgence. Then he lost it all in a hostile takeover. That collapse became the foundation for everything he teaches today. This conversation will challenge how you think about goals, discipline, and what it really means to perform at a high level — not just in one part of your life, but in all of them. What We Cover in This Episode * Boaz's leadership journey — from acting in New York, to building and taking a real estate company public, to losing everything in a hostile takeover * Life as a series of games — why every area of your life has its own rules, scoreboard, and time limit, and why that framework changes everything * Why top performers plateau — the real reason high achievers double down on their strengths instead of confronting their blind spots * The "inspiration junkie" trap — why waiting to feel motivated is keeping you stuck, and what to do instead * The 90-day framework — why 90 days is the sweet spot for building real, lasting change * Productive discomfort — why success was never meant to feel comfortable, and how to make peace with that * Trust and accountability — how misaligned goals quietly destroy trust on a team, and how to fix it * Why even the best need a coach — the humbling truth behind Steph Curry's shooting coach and what it means for the rest of us Key Quotes to Remember > "You don't need inspiration to do the work. You need to decide, and then you need a system that makes the decision for you." > > "The scoreboard doesn't care how you feel. It tells you if you're winning or losing — and that's the starting point for getting better." > > "You cannot change the rules in the middle of the game. You can adjust. You can get better. But the rules are the rules." > > "Success is not comfortable. Understand that, and then decide if you actually want it." A Few Questions to Sit With Boaz doesn't just hand you answers — he hands you better questions. Here are a few worth carrying into your week: 1. What game am I actually playing right now — and is it the one I say I'm playing? 2. Where am I doubling down on a strength instead of confronting a blind spot? 3. If a camera followed me for a week, would it capture the life I say I want? 4. Who's on my team right now — and are they built for the level I'm trying to reach next? About Boaz Gilad Boaz Gilad is an entrepreneur, author, and performance coach known for his work with high-achieving individuals and organizations. Born in Jerusalem, he served as a paratrooper in the Israeli army before moving to New York, where he studied acting at the Stella Adler Conservatory and philosophy at Hunter College. He went on to serve as CEO of several New York real estate development firms, playing a key role in Brooklyn's real estate resurgence and taking his company public. He's the author of The Real Estate Millionaire (McGraw-Hill) and The Zenith Code, has guest lectured in NYU's MBA program, and has been featured in The Wall Street Journal and The New York Times. He hosts the podcast Unmask and leads Zenith Clubhouse, a program for high performers pursuing growth across both business and life. Connect with Boaz: * Book: The Zenith Code [https://amzn.to/4gNrGGB] * Substack [https://substack.com/@boazgilad/posts] * Podcast: Unmask [https://podcasts.apple.com/us/podcast/unmask/id1801602344] * LinkedIn [https://www.linkedin.com/in/boaz-gilad-2237954/] * Learn more: zenithclubhouse.com [https://zenithclubhouse.com/] Free Learning To Lead Resources * Free Book: The Trust Gap [https://dl.bookfunnel.com/sair0nai5c] * The Learning To Lead Newsletter [https://www.markjcundiff.com/learning-to-lead-newsletter] * LeaderNotes [https://www.markjcundiff.com/leadernotes-register] 🔎 About LeaderNotes LeaderNotes [https://www.markjcundiff.com/leadernotes-register] is a quick-hit companion to each episode of The Learning to Lead Show. In just 5–10 minutes, Mark Cundiff recaps the top leadership insights, frameworks, and action steps from each interview, designed for busy, growth-minded leaders who want to review and apply the episode’s biggest takeaways on the go. It’s like the highlight reel + playbook—all in one. Contact Mark at: mark@markjcundiff.com

#63 Leadership Insights from my Conversation with Jennifer Doty

Free Learning To Lead Resources * Free Book: The Trust Gap [https://dl.bookfunnel.com/sair0nai5c] * The Learning To Lead Newsletter [https://www.markjcundiff.com/learning-to-lead-newsletter] * LeaderNotes [https://www.markjcundiff.com/leadernotes-register] 🔎 About LeaderNotes LeaderNotes [https://www.markjcundiff.com/leadernotes-register] is a quick-hit companion to each episode of The Learning to Lead Show. In just 5–10 minutes, Mark Cundiff recaps the top leadership insights, frameworks, and action steps from each interview, designed for busy, growth-minded leaders who want to review and apply the episode’s biggest takeaways on the go. It’s like the highlight reel + playbook—all in one. Contact Mark at: mark@markjcundiff.com

#62 You Don't Need All the Answers: Leading with Courage, Curiosity, and Confidence with Jennifer Doty

What if the biggest obstacle to your leadership isn't your experience—but the story you're telling yourself? In this episode of The Learning to Lead Show, Mark Cundiff sits down with Jennifer Doty, former Fortune 100 executive, speaker, author, and leadership coach, to explore how leaders can overcome self-doubt, embrace uncertainty, and create meaningful career and life pivots. Jennifer spent nearly two decades at MetLife, rising through multiple executive leadership roles. Along the way, she discovered that the best leaders aren't necessarily the smartest people in the room—they're the ones willing to ask better questions, learn quickly, and help others succeed. Together, Mark and Jennifer discuss overcoming imposter syndrome, leading outside your expertise, navigating career transitions, developing a resilient mindset, building powerful networks, and why changing your thinking is often the first step toward changing your leadership. If you've ever questioned whether you're ready for your next opportunity, this conversation will remind you that growth rarely begins inside your comfort zone. In this Episode You Will Learn * Why leadership is about influence—not expertise. * How Jennifer overcame months of imposter syndrome after taking on a role she knew nothing about. * The importance of mentors during seasons of rapid growth. * Practical strategies for navigating layoffs and major career transitions. * Why your identity should never be tied solely to your job title. * How daily mindset practices shape long-term leadership success. * Why asking better questions often matters more than having better answers. * The power of leading with gratitude and possibility thinking. * How customer-focused organizations avoid drifting away from what matters most. * Why limiting beliefs quietly sabotage leadership potential. * How leaders can reframe negative self-talk into empowering beliefs. * Why networking should begin long before you need your next opportunity. * Simple daily habits that build confidence, resilience, and emotional strength. Key Leadership Takeaways 1. You Don't Need Expertise to Lead Well 2. Growth Lives Outside Your Comfort Zone 3. Your Experience Is More Valuable Than You Realize 4. Ask Better Questions 5. Never Let Your Job Become Your Identity 6. Career Pivots Begin Long Before You Need Them 7. Be Clear About What You Really Want 8. Mindset Is a Daily Practice 9. Stop Believing Every Thought You Think 10. Put the Customer in the Room Memorable Quotes > * "You don't need to be the expert. You need to know the right questions to ask." > * "If I can do that, I can do anything." > * "Your relationships are one of the most valuable assets you'll ever have." > * "Your identity should never be your job title." > * "It's not happening to you. It's happening for you." > * "You get paid the same amount to be miserable as you do to be happy." > * "If you're going to make up a story, make up a good one." > * "Leadership is shining your light on others so they can see theirs." > * "It's always working out." Connect with Jennifer Doty Jennifer Doty is a former Fortune 100 vice president, speaker, author, and leadership coach who helps leaders and teams break through limiting beliefs, strengthen their mindset, and create meaningful, measurable change. Drawing from more than twenty years of executive leadership experience and her own career reinvention, she equips organizations and leaders with practical tools that transform confidence into action and mindset into lasting results. * LinkedIn [https://www.linkedin.com/in/jennifer-sierveld-doty/] * Website [https://livepure.com/] * Email: jenniferdoty0@gmail.com [jenniferdoty0@gmail.com] Free Learning To Lead Resources * Free Book: The Trust Gap [https://dl.bookfunnel.com/sair0nai5c] * The Learning To Lead Newsletter [https://www.markjcundiff.com/learning-to-lead-newsletter] * LeaderNotes [https://www.markjcundiff.com/leadernotes-register] 🔎 About LeaderNotes LeaderNotes [https://www.markjcundiff.com/leadernotes-register] is a quick-hit companion to each episode of The Learning to Lead Show. In just 5–10 minutes, Mark Cundiff recaps the top leadership insights, frameworks, and action steps from each interview, designed for busy, growth-minded leaders who want to review and apply the episode’s biggest takeaways on the go. It’s like the highlight reel + playbook—all in one. Contact Mark at: mark@markjcundiff.com

#61 Leadership Insights from my Conversation with Jon Dario

Free Learning To Lead Resources * Free Book: The Trust Gap [https://dl.bookfunnel.com/sair0nai5c] * The Learning To Lead Newsletter [https://www.markjcundiff.com/learning-to-lead-newsletter] * LeaderNotes [https://www.markjcundiff.com/leadernotes-register] 🔎 About LeaderNotes LeaderNotes [https://www.markjcundiff.com/leadernotes-register] is a quick-hit companion to each episode of The Learning to Lead Show. In just 5–10 minutes, Mark Cundiff recaps the top leadership insights, frameworks, and action steps from each interview, designed for busy, growth-minded leaders who want to review and apply the episode’s biggest takeaways on the go. It’s like the highlight reel + playbook—all in one. Contact Mark at: mark@markjcundiff.com

#60 Execution Beats Intention: How Great Leaders Turn Plans into Results with Jon Dario

Execution is not about having better intentions. It is about building better systems, stronger follow-up, clearer behaviors, and a culture where accountability helps people win. In this episode of The Learning to Lead Show, Mark Cundiff sits down with Jon Dario, author, speaker, management skills trainer, and creator of the AIM Framework: Action Item Management. Jon brings decades of leadership experience from major retail and service organizations, including Macy’s, Gap, Bank of America, and Travelex, and currently leads a real estate management company in the New York-New Jersey market.  Episode Summary What separates leaders who make plans from leaders who actually get results? That question sits at the center of this conversation with Jon Dario. Jon shares how his leadership journey began in retail management and how one honest conversation with an employee changed the way he saw leadership forever. Early in his career, Jon told a team member he did not have to work the same long hours Jon worked. The employee’s response was direct: “You can tell me that all day long, but your actions are what drives my behavior.” That moment helped Jon realize leadership is not just what you say. It is what you model. Throughout the conversation, Jon and Mark discuss the difference between management and leadership, why consistency builds credibility, why execution is often undervalued, and how leaders can use follow-up, feedback, and focused action to create more reliable results. This episode is a practical conversation for leaders who are tired of strategy sitting in binders, action items dying in meetings, and teams struggling with unclear priorities. About Jon Dario Jon Dario is an author, speaker, management skills trainer, and the creator of AIM, which stands for Action Item Management. His leadership background includes roles with some of the world’s most recognizable retail and service organizations, including: *  Macy’s  *  Gap  *  Bank of America  *  Travelex  Jon’s AIM system helps managers and organizations improve execution by clarifying actions, external influences, and desired results. His work focuses on helping leaders build systems, routines, follow-up rhythms, and cultures of accountability that produce consistent results over time. Key Ideas Discussed 1. Leadership Is Influence, Not Just Authority 2. Your Actions Drive Your Team’s Behavior 3. Follow-Up Is Foundational to Execution 4. Consistency Builds Credibility 5. The AIM Framework: Actions + External Influences = Results 6. When the Plan Gets Punched in the Face 7. Deciding Is Not the Same as Doing 8. High-Performing Teams Use the Same Language 9. Behaviors Fall Into Three Buckets 10. Accountability Is a Shared Obligation 📚 Resources Mentioned * AIM (Action Item Management) — Jon Dario [https://amzn.to/4vnd8RH] * The Slight Edge — Jeff Olson [https://amzn.to/4ezS0SW] * Atomic Habits — James Clear [https://amzn.to/4oVfipX] * Good to Great — Jim Collins [https://amzn.to/4eXnCky] * The Contrarian’s Guide to Leadership — Dr. Steven Sample [https://amzn.to/3SD8LEa] * Tiny Experiments - B. J. Fogg [https://amzn.to/4xVuOpK] 🎯 Connect with Jon Dario * LinkedIn [https://www.linkedin.com/in/jondario/] * Website [https://jondario.com/] * Email: jon@jondario.com Free Learning To Lead Resources * Free Book: The Trust Gap [https://dl.bookfunnel.com/sair0nai5c] * The Learning To Lead Newsletter [https://www.markjcundiff.com/learning-to-lead-newsletter] * LeaderNotes [https://www.markjcundiff.com/leadernotes-register] 🔎 About LeaderNotes LeaderNotes [https://www.markjcundiff.com/leadernotes-register] is a quick-hit companion to each episode of The Learning to Lead Show. In just 5–10 minutes, Mark Cundiff recaps the top leadership insights, frameworks, and action steps from each interview, designed for busy, growth-minded leaders who want to review and apply the episode’s biggest takeaways on the go. It’s like the highlight reel + playbook—all in one. Contact Mark at: mark@markjcundiff.com