Emotional Business

Olga Skipper
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  • Entrepreneurship
  • Updated Weekly

Emotional Business is a podcast for founders, creators, and change-makers who believe there’s more to business than spreadsheets and strategy. Hosted by Olga Skipper, this show explores the often-overlooked emotional undercurrent of entrepreneurship—highlighting how gut instinct, heart-centered decisions, and so-called ”illogical” paths can lead to powerful and profitable ventures. Through candid conversations with a wide range of guests—from top executives and tech leaders to unconventional entrepreneurs—Olga dives deep into what it really takes to build a business that not only makes money but feels meaningful. Listeners will walk away with a deeper understanding of how to: - Embrace emotions as a strength, not a liability, in business. - Make bold decisions based on inner truth, not external pressure. - Create a business model that truly fits who they are—and make good money doing it. This podcast is for anyone tired of cookie-cutter formulas and ready to explore success on their own terms.

  1. Season 3 Trailer

    Trailer Season 3 - Why Most Business Problems Are Relationship Problems

    Season 3 of Emotional Business centers around the following idea that many of the hardest business problems are really relationship problems. Executive coach Olga Skipper explores why founders become bottlenecks, why leadership teams struggle to function as real teams, and why so many CEOs feel isolated at the top. She breaks down the trust, conflict, control, and support dynamics that shape whether a company can truly grow. If you lead, build, or advise companies, this episode is a powerful reset on what it really takes to scale.

    Trailer Season 3 - Why Most Business Problems Are Relationship Problems

  2. May 25 ·  Bonus

    Human-First in an AI World: Leadership, Creativity, and Making the Leap with Alina Verbenchuk

    In this special bonus episode of Emotional Business, host Olga Skipper sits down with Alina Verbenchuk—co-founder of Korda, author, former Google and YouTube leader, and a passionate advocate for the creative economy. Alina Verbenchuk joins at a defining intersection: after a non-traditional journey into tech, years of scaling teams at major platforms, and the recent leap from corporate operator to founder. Together, Olga Skipper and Alina Verbenchuk unravel what remains deeply, stubbornly human in business and leadership—even as AI and automation touch every corner of work. This episode offers a candid, nuanced look inside the lived experience of building, leading, and selling in a world where originality and connection matter more than ever, but the landscape is shifting fast. In this episode, we explore: Creativity vs. Automation — Why human ideas, energy, and fresh perspectives are more valuable than ever as audiences grow weary of automated samenessThe Real Definition of “Human” — How genuine connection—whether in music, content, or business—is the foundation of resonance and trustFrom Non-Tech Background to Tech Founder — Alina Verbenchuk’s unique journey from studying Chinese, to business school, to building at Google, to boldly stepping into entrepreneurshipThe Messy Reality of Going Founder — The inner journeys, stumbles, and full-circle moments that rarely make it into founder storiesLeadership in Constant Change — Why templates and “typical” teams are breaking down, and what leadership needs to look like as companies and careers become more experimental and customizedSelling, Serving, and True Go-To-Market — Dismantling the myth of sales as a cold funnel; understanding it as a deeply human process of connection and valueAlina Verbenchuk and Olga Skipper move far beyond startup clichés to speak plainly about the fears, doubts, pivots, and exhilarating new definitions of ambition, value, and community. This episode is for any founder, builder, creative, or leader wrestling with how to stay human in a landscape being rewritten by technology. If you’re navigating the leap from secure roles to entrepreneurship, questioning where your real value lies, or curious how to build teams and markets for the future, you’ll find reassurance, clarity, and a lot of practical wisdom here. So settle in and enjoy this expansive, grounding, and deeply human conversation. Don’t forget to subscribe and share this episode with a founder or creative thinker in your circle! CHAPTERS 00:00 — Introduction to Emotional Business & Meet Alina Verbenchuk 01:04 — Alina Verbenchuk’s Non-Traditional Journey into Tech 02:50 — Why Human Creativity Rises as AI Grows 06:53 — Defining “Human” in Content, Business, and Beyond 09:58 — Full-Circle Lessons: From People Skills to Founder Strengths 14:12 — Human Connection at the Heart of Go-To-Market 17:06 — Purpose, Profit, and Serving People 19:32 — The Messy, Honest Leap from Corporate to Founder 27:00 — Beyond the Shelf: Leadership Now and Next 32:07 — What Leaders Need to Learn and Unlearn 34:20 — Generational Change, Agency, and New Teams 37:05 — Coaching Q&A: Teams of the Future and Personalization 44:39 — Who Do We Want on Our Team in an AI Era? 45:59 — Bringing It Full Circle: The Non-Linear Path of Leadership Connect with Olga: LinkedIn: Olga Skipper Website: www.olgaskipper.com Connect with Alina: LinkedIn: Alina Verbenchuk

    Human-First in an AI World: Leadership, Creativity, and Making the Leap with Alina Verbenchuk

  3. May 18

    Leading into the Unknown: Season 2 Reflections with Olga Skipper and Lana Khimka

    In this special finale of Emotional Business, Lana Khimka — fractional product leader for early-stage startups, organizer of ProductTank Berlin, and host of the Healthy Hedonism podcast — takes the host’s chair and guides Olga Skipper through a Season 2 debrief. The question behind the season was simple: What does it take to lead in 2026? After months of conversations with founders, executives, investors, and coaches, Olga and Lana step back to explore what is actually changing about leadership — and what surprisingly isn’t. How do leaders make decisions when there is no reliable playbook? How do you stay grounded when uncertainty becomes permanent? What matters more now: performance, resilience, pragmatism, relationships, or something else entirely? In this episode: What has — and hasn’t — changed about leadershipThe psychological weight of uncertainty and the growing scale of the unknownWhy resilience, grounding, and self-reflection are becoming core leadership skillsThe return of pragmatism: cash flow, sustainable business models, and reality checksWhy the people function and AI-driven cultural transformation belong on the CEO agendaWho thrives in uncertainty — and why identity outside work can become a source of resilienceMaking decisions without playbooks and learning to ask better questionsSomatic practices, journaling, alone time, and in-person connection as grounding toolsWhat leaders may need to unlearn: outdated planning models, self-evaluation frameworks, and unnecessary image-buildingHow technology is transforming coaching — and why human connection remains centralWhat’s next for Emotional Business in Season 3This is not a conversation about perfect answers or five-step frameworks. It is a pause to examine what it means to lead, live, and stay present when the future is difficult to predict. For founders, executives, coaches, and emerging leaders navigating change, this episode offers reflection, practical tools, and a different way of thinking about resilience and leadership. CHAPTERS 00:00 — Welcome & Season 2 Reflections 01:28 — The Intention Behind “Leading into 2026” 03:31 — What’s Changed for Leaders — and What Hasn’t 06:01 — Psychological & Emotional Pressures 08:37 — Essential Inner Shifts 10:58 — Pragmatism & Cash Flow 13:08 — The People Function in the Age of AI 17:08 — Who Thrives? Identity, Support & Doomsday Decisions 21:49 — Somatic Practice, Communication & Reality Checks 28:25 — What We Need to Unlearn 34:41 — Long-Term vs. Short-Term Planning 38:46 — Practical Grounding Habits 42:52 — The Future of Coaching & Technology 47:36 — What’s Next for Emotional Business Connect with Lana Khimka: LinkedIn: https://www.linkedin.com/in/lanakhimka/ Connect with Olga Skipper: LinkedIn: https://www.linkedin.com/in/olgasteidlskipper/ Website: https://www.olgaskipper.com/ Healthy Hedonism with Lana & Olga: https://open.spotify.com/episode/5l9joXoXourgs4ZPbtkPhI?si=q0hDoynoRa6tO04zED6_RA

    Leading into the Unknown: Season 2 Reflections with Olga Skipper and Lana Khimka

  4. May 11

    Anchoring with Intention: Boundaries, Networks, and Real Impact with Julia Derndinger

    In this episode of Emotional Business, host Olga Skipper is joined by Julia Derndinger — entrepreneur, advisor, and celebrated anchor for founders navigating the real terrain of business building. Julia’s approach isn’t about surface-level community or branding tactics. To her, network-building is infrastructure: it’s the trust, direction, and leverage that drive lasting outcomes for both her projects and those she supports. The conversation moves beyond platitudes about “community” and unpacks what actually creates ethical, reciprocal, impactful networks today. Olga Skipper and Julia Derndinger navigate the complexities of giving, the subtle differences between “community” and “network,” and how purposeful boundaries can empower entrepreneurs instead of holding them back. Tune in for insights not just on what’s changed in business since 2019 but what is required to succeed in 2024 and beyond. In this episode, we explore: Giving as a Core Identity — Why Julia doesn’t just help others, but finds deep joy (and even selfish joy) in doing so Network vs. Community — The nuanced distinction and why true impact goes far deeper than marketing buzzwords 05:01 Reciprocity and Boundaries — How to maintain generosity in a network while drawing necessary lines around energy and time 09:10 The Evolution of Leadership — How the most urgent and surprising founder topics have shifted since 2019 18:56 Building for Sustainability, Not Spotlight — Why Julia centers on profitability, well-being, and business health above hype Onboarding the Right People — How to join (and stay in) a high-trust network, and what disqualifies those seeking shortcuts 12:24 The New Reality of Teams and Generations — The challenges of recruiting, leading, and integrating Gen Y/Z in a fast-shifting business world 22:32 Personal Growth meets Professional Bravery — The inextricable link between self-development and business effectiveness, and what Julia now allows herself to bring into her work 30:02 This episode is for founders and advisors who want a grounded, honest look at the emotional labor and reward of anchoring ambitious, healthy, sustainable networks. If you’ve ever wrestled with boundaries, struggled to ask for your own needs, or wondered how to blend private grit and professional strategy, this conversation will resonate deeply. So drop in, and enjoy this raw, forthright, and practical exploration of anchoring with intention—no buzzwords required. Don’t forget to subscribe and share this episode with the real builders in your network! CHAPTERS 00:00 — Introduction to Emotional Business 00:02 — Meet Julia Derndinger: Builder, Sparring Partner, Giver 02:03 — Not Just a “Community Person”: The Origins of Julia’s Network 04:49 — The True Value and Fragility of Trust 08:31 — Why Give, Why Receive: Reciprocity and Boundaries 12:24 — Who Gets In: Onboarding to Julia’s Network 14:53 — Learning Boundaries the Hard Way 16:33 — The Real Cost of Unkept Boundaries 18:56 — Entrepreneurship and Leadership: The Shifting Landscape 22:02 — The Challenges of Growing Teams in 2024 25:02 — Female Founders, Scale, and Success on Your Own Terms 27:16 — When Personal and Professional Merge 31:44 — Final Reflections, Closing Gratitude Connect with Olga: LinkedIn: Olga Skipper Website: www.olgaskipper.com Connect with Julia Derndinger: LinkedIn: Julia Derndinger

    Anchoring with Intention: Boundaries, Networks, and Real Impact with Julia Derndinger

  5. May 4

    Scaling With Clarity: Leadership, Culture, and Founder Myths with Ivo Betke

    What happens to leadership when a company starts scaling faster than its internal playbook? In this episode of Emotional Business, Olga Skipper speaks with Ivo Betke — operator, advisor, and leader with experience scaling tech teams and building organizational culture. Together, they explore what growth does to clarity, culture, and leadership — and why founders often need to rewrite the way they lead as their organizations become more complex. In this episode: Why onboarding, shared context, and clarity matter more as teams scaleThe hidden cost of control — and why founders need to stop doing everything themselvesThe leadership myths in tech that create shame, pressure, and unrealistic expectationsWhy curiosity, listening, and making space for others are core leadership skillsHow talking time can reveal whether a leader is enabling ownership or becoming a bottleneckWhat a productive support culture actually looks like beyond perks and “good vibes”The tension between vision and operations — and why founders cannot bridge it alonePractical rituals for reflection and stepping out of reactive decision-makingHow teams can avoid featureitis, trend-chasing, and organizational chaosWhat executive coaching can — and cannot — do for leaders in scaling companiesThe role of ethics, responsibility, and technology in modern leadershipWhy founder experience, pressure, and unresolved patterns can shape the organizations they build Olga and Ivo move beyond startup clichés to examine what actually helps organizations grow without losing clarity, ownership, or humanity. This is a conversation about scaling as both an operational challenge and a leadership transition — from control to involvement, from individual answers to collective intelligence, and from founder instinct to organizational capability. For founders, startup operators, and tech leaders navigating growth, this episode offers practical ways to think about culture, ownership, reflection, and the role of leadership as complexity increases. CHAPTERS 00:00 — Introduction to Emotional Business 00:28 — Leadership Origins & Early Entrepreneurship 02:51 — Mission-Driven Teams & Cultural Learning 04:17 — Scaling Culture & Team Ownership 05:20 — Engagement, Vision & Context 08:02 — Letting Go of Control 09:58 — Curiosity & Making Space for Leadership 12:12 — Shame, Pressure & the Expert Trap 13:55 — Talking Time & Team Inclusion 16:27 — Balancing Direction & Consultation 17:37 — Bridging Vision & Operations 19:53 — Rituals for Reflection 22:01 — Featureitis, Trends & Culture Risks 24:26 — The Value and Limits of Executive Coaching 25:59 — AI, Job Change & Responsibility 27:55 — Ethics & Organizational Change 31:39 — Founder Trauma, Technology & Humanity 33:00 — Closing Reflections Connect with Ivo Betke: LinkedIn: https://www.linkedin.com/in/ibetke/ Connect with Olga Skipper: LinkedIn: https://www.linkedin.com/in/olgasteidlskipper/ Website: https://www.olgaskipper.com/ Subscribe to Emotional Business and share this episode with a founder or leader navigating growth.

    Scaling With Clarity: Leadership, Culture, and Founder Myths with Ivo Betke

  6. Apr 27

    Emotional Leadership, Diversity & Belonging with Konstantin Mihov

    In this episode of Emotional Business, host Olga Skipper sits down with Konstantin Mihov — a seasoned executive known for navigating the dynamic intersections of technology, people, and organizational culture. Together, they unpack the urgent realities of leadership in a changing world and dive deep into questions most companies are quietly struggling with: how do we foster real emotional connection and belonging inside organizations shaped by AI, automation, and rapid change? The conversation unfolds across personal anecdotes, practical examples, and hard-earned leadership wisdom, revealing what it takes to lead with emotional intelligence amid volatility and ambiguity. From the hunger for connection post-COVID to the evolving meaning of diversity, Konstantin Mihov shares his experiences forging belonging at scale and his candid reflections on the leadership paradigm shift: moving from answers to questions, from frameworks to genuine human presence. This episode brings you inside the emotional and strategic layers of co-creating culture, leading through uncertainty, and embracing the new realities demanded of leaders in 2026 and beyond. In this episode, we explore: • AI, Automation & Emotional Connection — how to scale human connection in organizations and where technology can help (and where it falls short) • Hybrid Work, Pandemic Aftermath & Hunger for Belonging — why in-person moments matter more than ever, and how leaders are adapting • The Leadership Paradigm Shift — why leading from questions (instead of answers) is essential and how to make ambiguity actionable • The Power and Pitfalls of Diversity — moving beyond gender to embrace broader definitions of diversity as a catalyst for innovation and adaptability • The “Bridge Commuter” Metaphor — leadership as boundary-spanning, and building genuine connections across geographies, functions, and cultures • Coaching, Vulnerability & Permission — what it really means to show up as yourself, challenge assumptions, and lead change without losing patience This episode is for executives, leaders, and culture builders who are navigating the messy realities of leading through transformation. If you’re wrestling with scaling connection, reframing diversity, or reinventing your leadership approach in a volatile world, you’ll find grounding, clarity, and practical takeaways here. So settle in and enjoy this candid, insightful exchange on emotional business, human connection, and leading from a place of authenticity. Don’t forget to subscribe and share this episode with a leader, teammate, or coach! CHAPTERS 00:00 — Introduction to Emotional Business 00:22 — Meet Konstantin Mihov: Leadership at the Intersection of Tech & People 01:03 — Why Connection & Diversity are Central to the New Leadership 01:29 — Navigating “Misfit” Status and Embracing Discomfort 02:46 — AI, Coaching & Building Connection at Scale 06:46 — The Post-COVID Hunger for Human Belonging 08:54 — Leadership in Ambiguity: Asking Questions, Not Just Providing Answers 17:15 — The Trap of VUCA/BANI: Beyond Frameworks to Intuition 19:05 — Getting Comfortable with Not Knowing, Bridging Cultures 26:12 — Diversity in Practice: Moving Beyond Black-and-White Thinking 33:07 — Coaching, Patience & Permission: Leading as Yourself 37:53 — Closing Thoughts Connect with Olga: LinkedIn: Olga Skipper Website: www.olgaskipper.com Connect with Konstantin: LinkedIn: Konstantin Mihov

    Emotional Leadership, Diversity & Belonging with Konstantin Mihov

  7. Apr 20

    Leadership Unlearning, AI Impact & Human-Centered Culture with Marius Hepp Kemper

    What do leaders need to unlearn when the old rules of success stop working? In this episode of Emotional Business, Olga Skipper speaks with Marius Hepp Kemper — serial entrepreneur, CEO of Junto, and a leader deeply engaged in the realities of organizational change. After building ventures, raising VC funding, and now bootstrapping a human-centered leadership development company, Marius brings a candid perspective on what happens when founders move from proving themselves toward building something more intrinsic, sustainable, and aligned. In this episode: Why the need to “prove yourself” can quietly shape founder decisionsWhat changes when leaders let go of external validation and choose markets, people, and goals differentlyMoving beyond VC narratives toward organic relationships and mission-driven growthWhat working with mid-market companies reveals about leadership developmentWhy practical expertise and long-term partnerships can matter more than startup hypeHow AI is changing organizations — and why emotional intelligence, self-reflection, and culture become more important, not lessWhat AI may replace in coaching and training, and where human experience still creates unique valueHow Junto is experimenting with personalization, measurement, and AI-supported leadership developmentWhy unlearning, humility, and a beginner’s mindset are becoming essential leadership capabilitiesThe return of entrepreneurial thinking and ownership inside larger organizationsHow gratitude and grounding can reshape the idea of “having it all” Olga and Marius explore the tension between technological transformation and human development — and what leaders need to preserve as organizations become more AI-enabled. This is also a conversation about identity: what happens when achievement is no longer enough, when external markers of success lose their power, and when leadership becomes less about proving and more about choosing. For founders, executives, people leaders, and anyone navigating organizational or personal transition, this episode offers a grounded perspective on growth, AI, ownership, and the practice of unlearning. CHAPTERS 00:00 — Leadership in Tech & Looking Toward 2026 01:13 — Entrepreneurial Roots & the Junto Story 04:35 — From VC to Bootstrapping 06:40 — Finding the Right Markets & Partners 10:18 — Lessons from Mid-Market Clients 11:02 — Human Transformation in the Age of AI 14:34 — Culture vs. Tech Adoption 15:55 — Coaching, Training & AI Substitution 17:11 — AI, Personalization & Measurability 19:33 — AI Roleplays & Skill Assessment 21:00 — Hybrid Teams & Human Skills 24:10 — Entrepreneurial Thinking in Corporates 25:46 — Unlearning & Beginner’s Mind 28:31 — Gratitude, Grounding & “Having It All” 33:04 — Closing Reflections Connect with Marius Hepp Kemper: LinkedIn: https://www.linkedin.com/in/mariushepp/ Connect with Olga Skipper: LinkedIn: https://www.linkedin.com/in/olgasteidlskipper/ Website: https://www.olgaskipper.com/ Subscribe to Emotional Business and share this episode with someone navigating leadership, AI transformation, or a major professional transition.

    Leadership Unlearning, AI Impact & Human-Centered Culture with Marius Hepp Kemper

  8. Apr 13

    Breaking the Inner Glass Ceiling: Leadership and Authentic Power with Dorothea von Wichert-Nick

    What happens when the biggest barrier to growth is no longer the market — but the leader? In this episode of Emotional Business, Olga Skipper speaks with Dorothea von Wichert-Nick — CEO coach, former MD/COO, and experienced advisor to founders and leadership teams. Dorothea works with what she calls the “inner glass ceiling”: the invisible limits shaped by personal history, beliefs, and recurring patterns that can become especially visible as a company grows. Together, Olga and Dorothea explore what happens when founders outgrow the leadership approaches that got them this far — and why sustainable growth often requires personal development, not just better strategy. In this episode: How fight, flight, and freeze can show up when leaders hit their limitsWhy personal growth often becomes a business issue as companies scaleHow early experiences and belief systems can shape ambition and leadershipHow founders can start recognizing their own “inner glass ceiling”Why self-development becomes increasingly important as responsibility growsDorothea’s “power within, power with, and power to” model for sustainable leadershipMoving away from pressure, isolation, and toxic hustle toward healthier growthWhy strong relationships and eye-level connection matter in leadershipThe difference between personal agency and leading through othersWhat founders should understand before starting a deeper coaching processWhy personal and collective transformation are connected Olga and Dorothea move beyond surface-level business advice to examine the internal dynamics behind entrepreneurial growth: the beliefs we carry, the ways we respond to pressure, and the leadership shifts required when organizations become bigger than the founder. This is a conversation about growing without simply pushing harder — and about building organizations that can thrive beyond one person’s energy, personality, or capacity. For founders, executives, and coaches interested in leadership development, scaling, and sustainable growth, this episode offers a thoughtful perspective on what it means to break through your own limits. CHAPTERS 00:00 — Introduction to Emotional Business 00:02 — Ambition, Limits & Leadership 00:06 — The Inner Glass Ceiling 00:08 — Scaling Companies & Ambitious Leadership 00:10 — Recognizing Your Own Limits 00:13 — What Makes a Great Coaching Client 00:15 — Hurdles & Resistance 00:17 — Preparing for the Coaching Process 00:20 — Power Within, Power With & Power To 00:24 — Dorothea’s Vision as a Coach 00:25 — Advice for the Coaching Community 00:28 — Recommended Resources & Models 00:29 — Closing Reflections Connect with Dorothea von Wichert-Nick: LinkedIn: https://www.linkedin.com/in/wichertnick/ Blog: https://www.volate.de/blog Connect with Olga Skipper: LinkedIn: https://www.linkedin.com/in/olgasteidlskipper/ Website: https://www.olgaskipper.com/ Subscribe to Emotional Business and share this episode with a founder or leader navigating their next stage of growth.

    Breaking the Inner Glass Ceiling: Leadership and Authentic Power with Dorothea von Wichert-Nick
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About

Emotional Business is a podcast for founders, creators, and change-makers who believe there’s more to business than spreadsheets and strategy. Hosted by Olga Skipper, this show explores the often-overlooked emotional undercurrent of entrepreneurship—highlighting how gut instinct, heart-centered decisions, and so-called ”illogical” paths can lead to powerful and profitable ventures. Through candid conversations with a wide range of guests—from top executives and tech leaders to unconventional entrepreneurs—Olga dives deep into what it really takes to build a business that not only makes money but feels meaningful. Listeners will walk away with a deeper understanding of how to: - Embrace emotions as a strength, not a liability, in business. - Make bold decisions based on inner truth, not external pressure. - Create a business model that truly fits who they are—and make good money doing it. This podcast is for anyone tired of cookie-cutter formulas and ready to explore success on their own terms.

Information

  • Creator
    Olga Skipper
  • Years Active
    2025 - 2026
  • Episodes
    38
  • Rating
    Explicit
  • Copyright
    © 2026 Olga Skipper
  • Show Website
    Emotional Business