The CEO Project Podcast

Is your business worth more when AI writes faster—or when you show up as an authentic leader your team actually trusts? You're under constant pressure to communicate clearly, move quickly, and keep up with AI without losing your voice in the process. In this episode, Jim Schleckser talks with Allison Shapira about the real tension leaders face today: using AI to gain efficiency while still sounding human, credible, and genuinely connected to the people who matter most. By listening, you'll gain: Clear guidance on how to use AI to strengthen your voice instead of diluting it as an authentic leader Insight into why AI-generated communication can quietly erode trust—and how to prevent it Practical ideas for balancing speed, clarity, and culture in leadership communication Hit play to discover how leading with authenticity—while using AI wisely—can increase trust, impact, and the long-term value of your business. Check out: 08:45 – Allison explains why AI-written emails can quietly destroy trust—and how leaders can spot when efficiency starts replacing authenticity. 22:10 – A practical breakdown of how to "train" AI to reflect your voice, values, and lived experience as an authentic leader. 41:30 – A cautionary story about leaders trusting AI over their team—and what it signals about culture, credibility, and leadership judgment. About Allison Shapira Allison Shapira is an executive advisor, Harvard lecturer, keynote speaker, bestselling author, and trained opera singer who helps senior leaders speak with confidence, clarity, and authenticity—especially in high-stakes, high-visibility moments. Since 2003, she has advised leaders from prime ministers to Fortune 50 executives and has designed leadership communication programs that drive trust, alignment, and measurable results. An entrepreneur and global expert in leadership and communication, Allison brings over two decades of experience to every engagement. Her practical frameworks integrate cutting-edge AI tools to help executives sharpen their message, amplify their voice, and Speak With Impact℠. An adjunct lecturer at the Harvard Kennedy School since 2015, her work has been featured in The Wall Street Journal, Bloomberg, The New York Times, and Harvard Business Review. She is the author of three books: the Washington Post best-seller Speak with Impact: How to Command the Room and Influence Others (HarperCollins Leadership), the companion e-guide Speak with Impact VIRTUALLY, and her newest book, AI for the Authentic Leader: How to Communicate More Effectively Without Losing Your Humanity (Spa Creek Press).

Have you thought about what your founder futures look like if you're suddenly not here—and whether your business worth is actually protected? You spend your time thinking about growth, valuation, exits, and risk—but many founders avoid the uncomfortable questions about legacy, control, and continuity. This episode connects estate planning to founder futures, showing how personal preparedness, governance decisions, and AI disruption all shape what really happens to the value you've built when circumstances change. By listening, you'll gain: A practical framework for protecting your founder futures by understanding how estate plans, healthcare directives, and digital assets prevent chaos for your family and your company. Clear insight into scaling a venture-backed platform the right way, including term sheets, preference stacks, board control, and why "IPO-ready" thinking matters more than chasing an IPO. A CEO's perspective on AI disruption and defensibility, including how category leaders must rebuild for an AI-native future before competitors force the change. Press play and learn how to safeguard your founder futures while building a company—and a legacy—that holds up under real-world pressure. Check out: ~06:30–09:30 Why estate planning matters even if you "don't have much" Cody explains why wills, healthcare directives, and digital assets matter regardless of net worth—and why certainty beats assumptions for families and founders. ~32:00–38:00 Venture capital reality: term sheets, preferences, and board control A candid CEO-to-CEO discussion on VC tradeoffs, preference stacks, governance, and why founders must be willing to walk away from bad terms. ~1:07:00–1:14:00 AI disruption and rebuilding to protect the business Cody outlines why AI is both the biggest threat and opportunity, and how Trust & Will is thinking about becoming AI-native before a challenger forces the change. About Code Barbo Cody Barbo is the Co-Founder & CEO of Trust & Will, the leading digital estate planning platform in the U.S., trusted by over one million families. Since launching in 2017, Trust & Will has modernized legacy planning with simple, secure, and attorney-approved online solutions tailored to state-specific laws. Under Cody's leadership, the company has raised over $75 million in funding, and its customers report more than $100 billion in estate assets on the platform. Trust & Will supports 20,000+ financial advisors and 200+ banks and enterprise partners, including AARP, Fifth Third Bank, UBS, and USAA. Recently, the company introduced EstateOS, the first intelligent estate planning platform designed to revolutionize legacy planning through embedded AI guidance, streamlined workflows, and enhanced collaboration between families and financial professionals. Trust & Will was recognized on the Inc. 5000 list for the second consecutive year in 2024. Cody was named an EY Entrepreneur Of The Year® 2023 Pacific Southwest Award Winner and regularly contributes to Forbes, Fast Company, and Inc. He is passionate about leveraging technology to transform estate planning from a transactional task into a deeply meaningful and personal experience.

Join Pete Foley, CEO of ModelOp and AI governance expert with over 25 years in enterprise software, as he dives into the challenges companies face with AI disruption. He discusses the critical need for AI governance and how to conquer production bottlenecks that can delay model deployment for months. Discover strategies to balance speed and risk, enhance visibility across AI projects, and ensure models translate into tangible business outcomes. Pete emphasizes the importance of a structured approach to scaling AI while protecting corporate integrity.

Ever catch yourself wondering, "What is my business worth—like, the real number, not the cocktail-party guess?" If your business represents the majority of your net worth (and for most CEOs, it does), not knowing your true valuation is risky. You could be planning an exit, thinking about succession, considering a partnership change, or even just trying to make smarter growth decisions—but without a real valuation framework, you're basically relying on back-of-the-napkin math. In this episode, you'll get a clear, CEO-friendly breakdown of how valuations actually work and what drives value up (or quietly drags it down). You'll walk away with: A practical understanding of the real valuation methods (market comps, public peer multiples, discounted cash flow, and when asset-based valuation applies) so you can stop guessing and start thinking like an investor. A sharper perspective on what increases or decreases your company's value—especially risk factors like customer concentration, shaky financials, key-person dependency, and unreliable forecasts. A clearer playbook for "valuation readiness" so you can improve value before a buyer, a partner, or the IRS forces the question. Press play now and steal the same valuation lens buyers use—so you can protect your wealth, reduce risk, and increase what your business is worth before the next big decision hits. Check out: 0:03:10 — The 3 main ways your business is valued (market comps, public peer multiples, and discounted cash flow—plus why valuation is forward-looking). 00:10:55 — How to value intangible assets like patents and trademarks (including the "relief from royalty" method that's surprisingly practical). 00:22:40 — The biggest value drivers you can actually control (clean financials, forecasting confidence, reducing key-person risk, and de-risking the business for buyers). About Dave Bookbinder Dave Bookbinder is a corporate finance executive with a focus on business and intangible asset valuation. Known as a collaborative consultant, Dave has served thousands of client companies of all sizes and industries. Dave has conducted valuations of the securities and intangible assets of public and private companies for various purposes including acquisition, divestiture, financial reporting, stock-based compensation, fairness and solvency opinions, reorganizations, recapitalizations, estate planning, S-Corp. conversion, exit strategy, and succession planning.

Megan Reilly, a successful entrepreneur and Shark Tank alumna, shares her journey of overcoming imposter syndrome. She recounts her experience as a D1 basketball walk-on, illustrating how self-doubt led her to quit prematurely. Megan discusses shifting from a side gig to a thriving franchise, emphasizing the importance of momentum over rigid planning. She highlights life’s seasonal challenges in balancing business and family. Packed with mindset tips, her insights inspire listeners to claim their seat at the table and embrace their value.

Karim R. Lakhani, a Harvard Business Administration professor and AI expert, shares insights on the rapid evolution of AI and its implications for businesses. He discusses how AI is lowering the cost of expertise, urging CEOs to adapt their business models for exponential growth. Karim highlights three new working modes—centaurs, cyborgs, and self-automators—that can help teams embrace AI without fear. He outlines a five-step playbook for CEOs to navigate this transformation, emphasizing the importance of caring for employees during this transition.

In this installment, Eric Vaughan, CEO of IgniteTech and an expert in AI-driven transformations, discusses the urgent need for businesses to adapt to AI, likening its impact to an 'iPhone moment.' He emphasizes that companies will split into 'haves' and 'have-nots' based on their AI adoption. Eric offers practical strategies for leaders to embrace AI as a creativity booster rather than merely an efficiency tool. He also addresses concerns about job displacement, advocating for continuous learning and upskilling to thrive in a rapidly evolving landscape.

Ever feel like your "new product" ideas stall out — not because they're bad, but because the team can't stay aligned long enough to bring them to life? If you're trying to grow in a world of constant AI disruption, you can't afford ideation that dies in committee or teams that melt down under pressure. This episode hits the real blocker most CEOs run into: brilliant people get promoted, but nobody ever taught them how to lead, think clearly under stress, or build a team that can take an idea from "interesting" to "in market." You'll hear how misdefined problems, ego-driven leadership habits, and check-the-box people programs quietly slow your growth — and what to do instead. A practical way to spot why ideas aren't turning into products (hint: it's usually a problem-definition gap, not a talent gap). A clearer read on your own leadership wiring — what's hardwired, what's learned, and how that mix impacts trust, communication, and execution. Simple, high-leverage moves to elevate your team's thinking so you can stop living in the tactical weeds and lead more strategically. Hit play now and steal Curtis Sprouses' tools for sharpening your team (and your own leadership) so your next big idea actually makes it to market — with fewer headaches and better results. Check out: 06:30 — The perfectionist founder example + why EQ can cap your growth Curtis walks through the real profile of a biotech CEO (high dominance, extreme perfectionism, low emotional intelligence) and shows how that combo derails fundraising, trust, and team performance — even when talent is off the charts. 18:45 — "Do you want to be remembered as the leader who grew people… or the one everyone avoided?" Curtis shares a sharp coaching story about a long-tenured exec who'd been rewarded for harsh habits for decades — and the one reframing that finally got him to shift how he led (with ripple effects at work and home). 28:00 — The #1 fatal flaw: CEOs define the problem wrong Curtis explains the "pressure vs. problem" distinction and gives a quick diagnostic (person vs. process vs. resources vs. priorities). This is the core "aha" for why teams spin and boards get frustrated. About Curtis Sprouse Curtis Sprouse is the founder of EurekaConnect and the Institute for Biomedical Entrepreneurship (IBE), where he helps leaders and teams outperform through strategic behavioral programs. With over 5,000 professionals coached and 200+ biomedical innovations advanced, Curtis specializes in turning science and technology into viable, impactful ventures. His programs have helped companies raise tens of millions in capital and bring real products to market. Curtis speaks on leadership, team building, personal development, and the future of business and society.

What if the real competitive edge in your company isn't another strategy shift—but your human sustainability as a leader? You're expected to perform like a high-level athlete: stay sharp, set direction, handle pressure, and keep your team moving—often while AI disruption speeds everything up. But here's the catch: if your internal system is running at red line, your decision-making, culture, and results eventually pay the price. In this episode, Jim Schleckser talks with Pearce Cucchissi, a former Army Ranger turned executive performance coach, about how leaders build the stamina, clarity, and resilience to thrive long-term—without burning out or becoming the bottleneck themselves. By listening, you'll gain: A fresh way to think about leadership as human sustainability—how to keep your mind and body durable enough for the pace you're running. Tools to identify "people bottlenecks" on your team, including what's really behind wrong-person/wrong-seat issues. A practical, data-informed approach (like psychometric assessments) to reduce stress deltas, improve fit, and increase longevity for you and your leaders—especially during growth or acquisitions. Press play to learn Pearce's battle-tested methods for building human sustainability into your leadership—so you can win the long game with more energy, focus, and staying power. Check out: 04:30 – "Business athlete" framing Jim and Pearce connect elite athletic performance to executive leadership—stamina, mental state, keeping score, and bringing the team along. 12:40 – Operator syndrome → CEO burnout bridge Pearce explains "operator syndrome" (stuck in fight-or-flight) and why the same pattern shows up in CEOs, athletes, and PE-backed exec teams. 24:10 – Psychometric delta + right person/right seat The Culture Index / psychometric "delta" idea: how to spot misalignment, stress, disengagement, and predict longevity—plus what to do with hotspots on a leadership team. About Pearce Cucchissi Pearce is a former military special operator who brings battlefield-tested strategic thinking and elite team dynamics to the boardroom. As the founder of Built to Evolve, he helps executives and teams unlock peak performance through a cutting-edge blend of neuroscience, psychology, and physiology. His mission is to create business athletes, leaders with the stamina, clarity, and resilience to thrive under pressure and deliver maximum positive impact. Pearce has worked with top-tier organizations including Citibank, The Las Vegas Raiders, and Charter Communications. Today, he advises executives within Private Equity-backed portfolio companies, where the stakes are high and the mental toll is real. His coaching style is direct, data-driven, and deeply human, balancing performance optimization with personal well-being to ensure leaders are built to evolve, not burn out.

Do you ever wonder why, no matter how much your business grows, your personal finances still feel out of control? If you've ever felt like your success at work doesn't translate to financial peace at home, this episode is your wake-up call. Jim Schleckser sits down with money expert and bestselling author Mike Michalowicz—creator of Profit First—to talk about why most people, even entrepreneurs, struggle with money and how simple behavior shifts can create real financial freedom. In this episode, you'll discover: How to "pay yourself first" in a way that guarantees profit instead of hoping for it. The behavioral money trap that keeps even smart business owners broke—and how to intercept it. A simple system to reduce financial stress for you and your employees, leading to happier, more productive teams. Hit play now to learn Mike's practical, life-changing approach to mastering your money habits—and start keeping more of what you earn today. Check out: [08:45] – The "Profit First" Mindset: Mike explains how reversing the traditional approach to profit—taking it off the top instead of waiting until the end—can transform how you run your business. [22:10] – The Behavioral Intercept: A powerful discussion on why most people fail with budgets and how simple systems at the bank level can automatically change your financial behavior for good. [39:25] – Redefining Retirement: Jim and Mike challenge the traditional idea of retirement and explore how to plan for a meaningful, flexible, and financially confident future. About Mike Michalowicz Mike Michalowicz is the entrepreneur behind four multi-million-dollar companies and the author of bestselling business books including Profit First, Clockwork, The Pumpkin Plan, and All In. His newest book, The Money Habit, is a groundbreaking approach to personal finance. The television host of The 4 Minute Money Maker and a former columnist for The Wall Street Journal, Mike now travels the world helping individuals grow thriving businesses and live richer lives.