Free The CEO

Hosted by Kahlil Dumas

Business Entrepreneurship EducationInterviews guests

Episodes

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About the show

Welcome to the Free The CEO Podcast—the go-to show for founders, solopreneurs, and fractionals who want to lead with vision, not get stuck in the weeds. Get expert insights, real-world strategies, and battle-tested tactics to help you create a business that runs smoothly through smart systems and strong teams.

Listen to episodes

60 recent

18 min

EP #92: Beyond AI: The Critical Role of Human Expertise in Tech Innovation

In today's episode, I'm answering that question burning in everyone's inbox: "How is AI going to impact my job?"As someone working with both startups and Fortune 500s, I wanted to bring you the employer's perspective on this incredibly nuanced topic.The truth?While technological advancement is accelerating at a pace that would make your head spin, companies are facing a critical challenge—they have amazing tech but lack employees who can actually leverage it.Connect with me on LinkedInWork with my fractional firmWork with my executive search and advisory firmConnect with our panelists

27 min

EP #91: Why Diverse Leadership is Non-Negotiable for Startup Success (Execnow Linkedin Live)

In this Execnow Linkedin Live, we’ll explore why talent diversity is essential for you as a startup, the common hiring pitfalls you face, and actionable strategies to leverage inclusivity and build diverse, high-performing teams.Connect with me on LinkedInWork with my fractional firmWork with my executive search and advisory firmConnect with our panelists

33 min

EP #90: The Business Case for DEI: What CEOs Need to Know About Pulling Back

In this episode, we dive deep into the pushback against Diversity, Equity, and Inclusion (DEI) and its true business impact. Our panelists—Ayanna King, Abby Adamson, and Colin—discuss the reality of DEI rollbacks, the myths surrounding meritocracy, and how leaders must be held accountable for real change.What You’ll Learn in This Episode:Why DEI backlash is happening and how we got hereThe business case for DEI and why it’s not just a trendHow performative actions have replaced real commitmentsWhy neutrality is complicity—and what leaders must do insteadHow companies can avoid short-term thinking and invest in DEI for long-term successConnect with me on LinkedInWork with my fractional firmWork with my executive search and advisory firmConnect with our panelists

33 min

EP #89: Emotional Intelligence, AI, and the Future of Content Marketing with David Baum

In this episode, I dive into the power of emotional intelligence and AI in leadership and content marketing. David Baum, a seasoned founder and investor, shares how empathy-driven leadership and building in public have shaped his startup, Relato. We explore the role of AI in content creation, its limitations, and how human connection remains irreplaceable in storytelling.David also breaks down product-market fit, the importance of user research, and how bold leadership helps founders navigate uncertainty.What You’ll Learn in This Episode:How emotional intelligence sets great leaders apart.The balance between AI and human creativity in content marketing.Why building in public is a game-changer for startups.How David identified product-market fit signals at Relato.The biggest mistakes founders make in early-stage growth.LinksConnect with me on LinkedInWork with my fractional firmWork with my executive search and advisory firmConnect with David Baum

20 min

EP 88: Engineering the Future: AI, Policy, and Inclusive Technology with Ishvaraus Davis

In my conversation with Ish, we explored his journey from Southeast Georgia to becoming an engineering leader in Silicon Valley. Starting with computer science at the University of Pittsburgh, Ish shared how a college startup project led to his recruitment at Meta, where he worked on B2B advertising algorithms. His career path included roles at IBM, where he learned business fundamentals, and later a shift to tech policy work in Congress, focusing on emerging technologies like quantum computing and AI.LinksConnect with me on LinkedInWork with my fractional firmWork with my executive search and advisory firmConnect with Ish Davis

25 min

EP #87: Unleashing Team Potential & Beating Founder Burnout with Jhana Li

We are back—rebranded as Free The CEO! This pivot perfectly aligns with my current work and lifestyle. While UNSTUCKKD will always be my launchpad, Free The CEO now represents my fractional firm and solopreneur business, along with Execnow, my executive search firm.In this new chapter, I'll be interviewing founders, CEOs, and visionary leaders—diving deep into their journeys, insights, and the innovative strategies that drive their success. Learn more about these exciting ventures through the links below.In this episode, I chat with Jhana, founder of Spyglass Ops, about her journey in mastering operations and scaling businesses efficiently. Mentored early on by Leila Hormozi, Jhana discovered her talent for spotting inefficiencies and creating robust systems—skills that have helped hundreds of startups free founders from daily operational tasks and drive sustainable growth.LinksConnect with me on LinkedInRegister for Solo Summit Presented by Lettuce Financial Work with my fractional firmWork with my executive search and advisory firmWork with Spyglass Ops

18 min

EP #86: The Rise of the Fractional Executive with Kahlil Dumas

In this episode, I explore the rapid growth of fractional executive roles, which have expanded from 2,000 to over 125,000 on LinkedIn in just a few years. I break down how fractional execs go beyond traditional consulting to drive real results.Sharing my own journey into fractional leadership after a layoff, I discuss how it boosted my income and gave me the flexibility I needed as a new dad to twins. This experience led me to launch Execnow, a platform connecting companies with diverse fractional talent.I’m here to guide both companies and executives into this exciting shift – because the future of work is fractional.What You’ll Learn in This Episode:The exponential growth of fractional executive roles and what it means for the future of work.Key distinctions between fractional executives and consultants.Kahlil’s personal journey into fractional leadership, from layoff to lifestyle shift.The benefits of fractional executives for companies and for leaders seeking flexibility.How Execnow aims to bring more diverse talent into early-stage leadership roles.Why diverse teams consistently outperform non-diverse teams by 35%.LinksConnect with Kahlil on LinkedInLearn about Execnow: Hire Diverse Talent

31 min

EP #85: The Intuitive CEO with Sabrina Guler

In this episode, we sit down with Sabrina Guler, former engineering project manager at Apple, turned successful entrepreneur and co-founder of an eight-figure business. Sabrina opens up about her decision to leave corporate life, the fears she faced, and how listening to her intuition guided her through the transition.We explore the power of transformation, the importance of aligning intention with action, and how embracing discomfort can lead to growth. Sabrina also shares her unique perspective on integrating spirituality in business, defining it as "coming back to your truth," and highlights the role of self-trust in entrepreneurial success.What You’ll Learn in This Episode:Sabrina’s journey from corporate life at Apple to entrepreneurship.How to listen to your intuition and take the leap despite fear.The role of transformation and why discomfort is necessary for growth.Aligning your actions with your true purpose for better outcomes.Spirituality in business: how self-trust and authenticity fuel success.Insights into Sabrina’s six-week cohort program for business and personal growth.LinksConnect with Kahlil on LinkedIn!Free The CEOExecnow: Hire Diverse TalentConnect and Learn from Sabrina

29 min

EP #84: The Highs, Lows, and Lessons of Going All-In on a Startup with Jack Beckwith

In this episode of Free the CEO, we chat with Jack Beckwith, founder and CEO of The DataFace, a leading data visualization and storytelling agency.Jack talks about his journey from analyst to CEO, overcoming startup challenges, and how side projects can evolve into thriving businesses. Listeners will gain valuable insights on:The Power of Side Projects: How Jack’s passion for data evolved from a blog in college to a full-fledged agency.Taking the Leap: What led Jack to leave his job and go all-in on his own business.Finding Clients and Scaling Smartly: Jack’s experience landing major clients like Yelp and Universal Music Group and how cold outreach played a pivotal role.Navigating Business Models: The pros and cons of hourly, fixed-fee, and retainer models, and how The DataFace found its niche.Setting Boundaries as a CEO: Why saying “no” helped Jack grow his business.Maintaining Balance: Tips on prioritization, empowering your team, and keeping work-life harmony as a founder.LinksConnect with Kahlil on LinkedIn!Free The CEOExecnow: Hire Diverse Talent

6 min

EP #83: Double the Joy: Welcoming Twins & New Beginnings with Kahlil Dumas

And Just Like That, We’re Back!After a nearly three-month break, we’re back in full force! In this episode, I open up about what’s been happening during this hiatus, including the life-changing arrival of my identical twin boys, Braxton and Beau. I share reflections on parenthood, personal growth, and the exciting expansion of both ExecNow and Free The CEO. It’s been a wild ride, and I'm excited to reconnect with you all, dive back into providing valuable content, and share updates on the journey ahead.Links & Resources:Follow me on LinkedIn and Instagram for the latest updates.Check out Execnow for executive placement services.Learn more about Free The CEO and how we help founders scale their businesses.