Startup CEO Succession

Nate Tucker, founder of Start Playing Games — the marketplace for professional game masters where GMs have earned over $50 million — joins Evgeny to share his journey from a YCombinator tar pit idea through a COVID pivot to building a profitable, category-creating platform backed by Andreessen Horowitz.Their conversation covers the serendipitous discovery of his co-founder Devon, the painful lessons of scaling culture and hiring too fast, learning to trust his gut alongside disciplined decision-making, and the eight-month process of planning and executing his CEO succession — handing the reins to Devon while ensuring the company thrived without him. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit substack.evgeny.coach

Nic Brisbourne, senior partner at Molten Ventures, and Evgeny Shadchnev talk about their experiences with CEO transitions in startups. They discuss the complexities and risks involved in changing a CEO in a VC-backed business, sharing personal stories and lessons learned from their decade-long professional relationship.00:00 Introduction02:14 How Not To Force Out a CEO09:12 The Risks Of Removing a CEO10:52 Selecting the Right Successor14:59 We'll Invest If You Step Down19:58 CEO Transition at Makers27:05 Key Factors for a Successful Transition32:00 How To Start Discussing a CEO Succession39:42 CEO Performance vs Company Performance41:25 Advice for Founders and Investors49:01 Final ReflectionsLearn more about Evgeny's work as a CEO coach: https://www.evgeny.coachStartup CEO Succession: a Founder's Guide to Leadership Transition is available on Amazon: https://www.amazon.co.uk/dp/B0CW1HLZTR  This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit substack.evgeny.coach

Jerry Colonna changed my life as a leader.I first met Jerry at his CEO Bootcamp in the Colorado Rockies in 2015. As a newly minted CEO, I joined a small group of founders hosted by Jerry and his team on a stunning ranch. It was my first coaching experience.Those five days profoundly shifted my trajectory as a leader. It's difficult to capture exactly what happened there, but I began learning how to lead from the heart, not just the head.Jerry and I became friends. His books, Reboot and Reunion, have deeply touched me and many of my friends. When I stepped down as CEO of Makers in 2020, I chose to train as a founder coach myself, inspired by his impact.Later, Jerry generously wrote the foreword to my book, Startup CEO Succession, sharing reflections from our journey together. In this special conversation, we explore CEO successions, why pursuing wholeness matters more than chasing happiness, and why inner work is a lifelong adventure.Enjoy the episode!Timestamps(Clickable on Youtube)00:00 Introduction02:32 Over-Identification with Work07:23 True Self and False Self15:00 This Suffering is Avoidable27:28 "I'm 61. It took 60 years, you know?"33:59 Wisdom Practices40:04 Love, Safety and Belonging48:22 Letting Go vs Giving Up53:10 Standing Still When Your Hair Is On Fire56:14 Challenges That Are Not Ours To Face01:00:25 Successful CEO Transitions01:09:07 Final Reflections This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit substack.evgeny.coach

Matt Colebourne, a seasoned entrepreneur and professional CEO with over 30 years of experience, joins Evgeny to discuss the critical decision founders face about whether to continue leading their business or bring in new leadership.Matt shares his journey, which includes starting and selling an AI company in the mid-nineties and turning around and exiting five other companies since.Their conversation covers the importance of self-awareness and soft skills in leadership, practical challenges in growing and scaling technology businesses, and the nuanced decisions around CEO succession and leadership transitions. 00:00 Introduction01:53 Matt Colebourne's Career Journey07:07 Replacing Founder CEO at Searchmetrics17:06 Stepping Down vs Compensating for Weaknesses22:36 Transforming Searchmetrics26:52 Product Features vs Customer Needs32:47 Turning around Qwist Group39:34 Advice for Founders, CEOs and Investors53:53 Final ReflectionsLearn more about Evgeny's work as a CEO coach: https://www.evgeny.coachStartup CEO Succession: a Founder's Guide to Leadership Transition is available on Amazon: https://www.amazon.co.uk/dp/B0CW1HLZTR  This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit substack.evgeny.coach

Judit Petho, a seasoned executive with a multifaceted career spanning roles as a lawyer, global CEO, and startup leader, joins Evgeny to discuss her journey from corporate law to leading one of the world's largest consultancy firms, and then to turning around and scaling startups. She emphasises the importance of adaptability, understanding business resources and people management at different levels of company scale. Judith shares insights on the critical role of soft skills in leadership, the challenges of managing investor relations and transformation projects, and the evolving dynamics of leadership in remote and hybrid work environments. 00:00 Introduction01:05 Judit's Professional Background09:32 Fixed vs Beginner's Mindset15:01 CEO: Same Title, Three Different Jobs18:17 Role of a COO24:03 The Job of a CEO34:10 The Importance of Soft Skills44:11 The Importance of Listening47:17 Building Soft Skills in a Hybrid World58:34 Final ReflectionsFind Judit Petho at juditpetho.com.Learn more about Evgeny's work as a CEO coach: https://www.evgeny.coachStartup CEO Succession: a Founder's Guide to Leadership Transition is available on Amazon: https://www.amazon.co.uk/dp/B0CW1HLZTR  This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit substack.evgeny.coach

Dhruv Ghulati, founder and former CEO of Factmata, a startup focused on tackling misinformation using AI, shares his in-depth journey from founding the company to stepping down as CEO. We discuss incentivising early-stage team members, the challenges faced by solo founders, and the critical moments of product pivots and funding struggles. Dhruv also talks about his decision to hire a successor CEO, leading to the eventual acquisition of Factmata, and reflects on his transition from startup life to roles in larger companies like Onfido and Uber.00:00 Introduction01:35 Factmata's Early Days05:14 Equity for Early Team Members10:45 Fundraising for a Pivot20:15 Fundraising as a Solo Founder24:21 Delegating to the Team30:41 Constant Fundraising36:59 Finding a Replacement CEO38:56 The Second Attempt to Hire a CEO44:05 Next Steps After Factmata46:16 Preparing for Acquisition52:54 Post-Exit Reflections and Career Transition01:02:42 Final ReflectionsLearn more about Evgeny's work as a CEO coach: https://www.evgeny.coachStartup CEO Succession: a Founder's Guide to Leadership Transition is available on Amazon: https://www.amazon.co.uk/dp/B0CW1HLZTR This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit substack.evgeny.coach

Evgeny Shadchnev interviews Neal Gandhi, founder and ex-CEO of TPXimpact. Gandhi shares his journey of leading TPXimpact from a small Bulgarian company to a public entity with £90 million in revenue in just five years. The discussion covers the challenges of hyper growth, the importance of planning for extreme success, and the complexities of CEO succession. Gandhi reflects on the strategic decisions, the role of self-awareness, and the importance of building a strong senior management team to complement a founder's strengths.00:00 Introduction01:29 Neal Gandhi's Entrepreneurial Journey05:36 Stepping Down as CEO09:17 Navigating the CEO Transition14:35 Running a Business in Hyper-Growth Mode16:57 "Honestly, It Was a Surprise"22:49 Choosing a Successor25:54 Do CEOs Have to Step Down?28:52 What Could Have Gone Differently?38:47 Transition to New Leadership41:50 Next Steps45:18 Advice for Founders and CEOs50:14 Advice for Boards55:28 Public vs. Private Company CEO Succession58:48 Final ReflectionsLearn more about Evgeny's work as a CEO coach: https://www.evgeny.coachStartup CEO Succession: a Founder's Guide to Leadership Transition is available on Amazon: https://www.amazon.co.uk/dp/B0CW1HLZTR  This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit substack.evgeny.coach

James McAulay, founder of Encore, a marketplace for booking live music bands and Evgeny Shadchnev discuss James’ journey of leaving the business. James shares his transformative experience of taking a two-month sabbatical that helped him overcome burnout, successfully sell his company, and promote an insider to lead it. Now poised to join ElevenLabs, a leading AI company, James delves into his personal journey of meditation, running, and mental wellness.00:00 Introduction02:13 The Journey of Encore05:16 Startup Challenges and Burnout07:03 The Sabbatical Decision12:13 Preparing for Succession18:43 Returning to Encore23:52 Meditation and Mindfulness32:43 The Power of Running35:10 Choosing to Step Away from Encore40:43 Choosing the Next Step44:51 Joining Eleven Labs51:40 Advice for Founders58:14 Final ReflectionsThe blog post about running that was mentioned: https://jamesmcaulay.co.uk/running-with-spirit/ Learn more about Evgeny's work as a CEO coach: https://www.evgeny.coachStartup CEO Succession: a Founder's Guide to Leadership Transition is available on Amazon: https://www.amazon.co.uk/dp/B0CW1HLZTR  This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit substack.evgeny.coach

Evgeny Shadchnev discusses the complex journey of CEO transitions in venture-backed startups with Maria Josife, a partner at the executive search firm Erevena. They delve into the triggers for considering a CEO change, how to approach the process strategically, and the importance of starting conversations early.00:00 Introduction01:32 About Erevena04:15 The Complexities of CEO Succession in Venture-Backed Startups08:50 Replacing vs Augmenting a Founder CEO11:01 Starting the Conversation Early16:19 The Timeline and Process for a Smooth CEO Transition22:41 The Role of Coaches, Chairs, and Non-Execs in CEO Succession26:17 Hire Right to Remain as CEO33:50 The Drivers of Success of CEO Change37:17 The Risks of Hiring with Intent to Promote to CEO39:58 First-time CEOs vs Experienced CEOs42:14 Insiders vs Outsiders44:12 What Happens to Founder CEOs After They Step Down47:36 Advice for Founders And Investors56:38 Key TakeawaysLearn more about Evgeny's work as a CEO coach: https://www.evgeny.coachStartup CEO Succession: a Founder's Guide to Leadership Transition is available on Amazon: https://www.amazon.co.uk/dp/B0CW1HLZTR  This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit substack.evgeny.coach

Avin Rabheru, the founder and CEO of Housekeep, talks to Evgeny Shadchnev about navigating a CEO succession. They discuss the challenges founders face in transitioning to professional leadership. Avin shares insights into the inflexion points in a company's growth, when founders might consider stepping down, and emphasises the importance of continuous learning for founders.00:00 Introduction03:31 Most Founders Think They're Great07:30 Two out of Three Times Founders Are Pushed Out09:47 Inflection Points in Business Growth19:04 Could Someone Run Housekeep Better?21:51 Balancing Leadership and Personal Life25:16 Roles of Founder and CEO at Housekeep29:48 What Founders Bring To The Table32:51 Why Most Founding Teams Get Replaced36:08 Identifying Strong Founders42:37 "I Encourage All Founders To Just Keep Going"50:42 A Fundamental Betrayal53:16 Final ReflectionsLearn more about Evgeny's work as a CEO coach: https://www.evgeny.coachStartup CEO Succession: a Founder's Guide to Leadership Transition is available on Amazon: https://www.amazon.co.uk/dp/B0CW1HLZTR  This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit substack.evgeny.coach