Startup CEO Succession

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

Graham Hobson, founder of Photobox, Europe’s largest personalisation company, and Evgeny Shadchnev explore Graham's decision to hand over leadership to an external CEO as Photobox began to scale. Graham discusses the challenges and benefits of this transition, sharing his experiences with burnout and recovery. Additionally, they delve into Graham's advocacy work with Patriotic Millionaires UK, focusing on wealth taxation and social responsibility.00:00 Introduction01:59 Should We Tax Wealthy People More?12:53 The Early Days of Photobox18:18 A Merger with a Competitor22:11 The Toughest Boss I Ever Had29:13 Being Part of an Executive Team30:00 Challenges That Shape Us35:04 When To Go Fast and When To Go Slow37:33 Advice To Own Son41:36 Advice To Other Founder CEOs46:26 Fresh Eyes Exercise for Leaders51:02 Final ThoughtsLearn 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 transition of leadership at Makers, a tech talent and training platform, with Claudia Harris, who succeeded him as CEO. They reflect on their journey, starting from Claudia's initial role as chair of the board through the challenges posed by the COVID-19 pandemic, and the critical steps in the handover process. Claudia shares insights into managing the transition and the importance of doing work you love.00:00 Introduction01:47 What is Makers?03:58 From Chairman to CEO of Makers06:36 The Initial Conversations About Succession11:13 The Decision to Change the CEO18:35 Navigating the Pandemic22:59 The Handover Process31:12 First Crisis as the New CEO35:11 Biggest Lessons39:25 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

Henrik Hagemann, founder and former CEO of Puraffinity, joins Evgeny Shadchnev to explore Henrik's journey from founding the company to realising the need for a new CEO to take the business to the next level. Henrik discusses the challenges of making the decision together with the board, the rigorous executive search process, and how to handle the emotional and practical aspects of stepping down. They also delve into the importance of maintaining multiple personal identities outside the CEO role, the future vision for Puraffinity and Henrik’s new role.00:00 Introduction01:42 About Puraffinity04:53 Henrik's Role as Founding CEO08:57 The Decision to Step Down as CEO23:30 The Search for a New CEO35:57 Inclusive Hiring and Psychometrics Tools39:36 Zeroing in on the Successful Candidate42:16 Handover and Onboarding46:29 Transitioning from CEO to New Role51:29 Transition Lessons and Next Steps56:56 Advice to Other Founders01:01:30 Final ThoughtsLearn 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

Alicia Navarro, founder and ex-CEO of Skimlinks, takes us through her journey from founding Skimlinks and building it into a leading content monetisation platform to making the tough decision to step down as CEO after 11 years and promote one of her senior leaders to the CEO position. Two years later, the new CEO successfully exited the company. Alicia and I discuss the difference between founder-CEO and scale-up CEO in the context of preparing to sell a VC-backed business.00:00 Introduction01:38 Founding Skimlinks05:53 Deciding to Step Down as CEO10:22 The Transition Process and Board Dynamics15:02 Physical and Emotional Toll of Leadership17:12 0-to-1 Founders and 1-to-N Founders22:08 Post-CEO Work as President23:45 Power Handover29:02 Team Reactions and Culture Shift30:48 Post-Transition Success33:20 Reflecting on Leadership and Lessons Learned37:35 Board's Role in the Transition39:05 Life After the Exit41:22 Advice for Founders and Future CEOs49:46 The Importance of Succession Planning51:32 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

Øyvind Reed, the founder and ex-CEO of Whereby, recounts his journey of building and leading a global video conferencing company from a small Norwegian town, navigating explosive growth during the pandemic amidst intense competition from global giants, before deciding to step down as the CEO.00:00 Introduction01:43 The Founding Story of Whereby03:35 Growth During the Pandemic09:53 The Decision to Step Down as CEO14:55 Transitioning the Leadership20:43 Involving the Board30:00 Internal vs External Candidates32:28 Executing the CEO Transition Plan33:51 The Emotional Impact of Stepping Down35:10 Transition Timeline37:52 Becoming the Executive Chair38:59 Balancing Family and Professional Life43:28 Finding the Next Professional Step45:54 Being a Founder CEO vs. Hired CEO47:34 Impact on the Family49:47 Post-Transition Reflections56:36 Advice for Founders and Investors01:00:51 Closing ThoughtsLearn 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

Nic Yeeles, VP of Product at Resi, and Evgeny Shadchnev discuss Nic’s journey from founder and CEO of several businesses to transitioning into a VP of Product role at another startup. The conversation delves into Nic’s strategies for rebranding himself for the VP of Product role and his experiences as the right-hand man of different CEOs. He emphasises the value a former founder brings to a startup, the importance of 'fake it till you make it,' and the transformative power of resourcefulness.00:00 Introduction02:30 Founding and Exiting Peg04:54 Founding a Climate Impact Startup08:16 Trying a Consulting Role11:16 The Ex-CEO Advantage13:42 Choosing the Next Career Step17:47 Interviewing for a Role You Never Performed22:51 Navigating Cultural Alignment25:44 Power of Personal Networks28:07 Joining Resi as a VP Product31:12 The Challenge of Identity Shift32:53 Working with Non-Founder C-Level Executives35:21 The Value of Entrepreneurial Skills37:04 The Costs of Not Starting Another Business38:34 Choosing Startups Over Large Companies40:39 Considering Freelance and Advisory Roles41:53 Lessons Learned53:34 Hiring Ex-entrepreneurs58:03 Final Thoughts and 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. 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

Jamie Undrell, founder and chair of SaveMyExams, and Evgeny talk about Jamie’s journey from founding the company to stepping down as CEO in March 2024 in favour of his trusted COO, Constance. We discuss balancing intuition and rational analysis behind the decision, the differences between leading a bootstrapped versus a venture-backed company, the merits of an internal successor, and Jamie's new role and future plans. (Disclaimer: Evgeny coached Jamie through this CEO transition.)00:00 Introduction01:46 Founding Story of SaveMyExams03:35 The Decision to Step Down as CEO05:57 Starting the Transition Early09:01 Mitigating Fears and Concerns10:59 Internal Vs External Candidates15:15 Adjusting to the New Role as Chair17:00 Impact on the Team and the Business19:25 Personal Reflections and Advice for Founders30:24 Future Plans32:38 Conclusion and 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. 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

Simon La Fosse founded La Fosse Associates, a leading IT talent solutions agency, in 2007. Since then, he has appointed two CEOs, and both CEO transitions have been successful, as evidenced by the growth of the business: almost £200m in revenues and nearly 500 employees.Simon and Evgeny discuss the importance of recognising one's limitations and the complexities involved in transitioning leadership roles within a company. Simon shares his experience of promoting internal talent over external hires, turning La Fosse into an employee-owned company, and maintaining company values during challenging times.00:00 Introduction03:08 Founding La Fosse Associates05:40 Core Values: Co-Ownership and Care10:24 Upholding Values During Hard Times14:34 First CEO Transition20:08 Navigating an Inflection Point23:41 Second CEO Transition27:11 Trusting Founder's Intuition29:52 Developing a People-First Culture31:20 Simon's Next Chapter33:46 An Ecosystem of Support36:21 Balancing Work and Life40:55 Advice for Future Founders47:44 Final Reflections and TakeawaysEvgeny Shadchnev is a founder coach who works with entrepreneurs and CEOs to ensure smooth CEO successions. Find out more about his work at www.evgeny.coach.Startup CEO Succession: a Founder's Guide to Leadership Transition is out now. Find it on Amazon. 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

Gretchen Lennon, founder of Lennon Legal, joins Evgeny Shadchnev to discuss key legal aspects of CEO succession.We explore the importance of obtaining independent legal advice, understanding good and bad leaver provisions, negotiating settlement agreements, the potential tax implications tied to shares and share options, and more.Timestamps00:00 Introduction02:31 Hypothetical CEO Resignation05:06 Unfair Dismissal08:12 Shares,  Options and Taxes16:36 Getting Legal and Tax Advice18:37 Negotiating Settlement Agreements21:59 Post-Termination Restrictions26:42 Staying with the Business as an ex-CEO32:16 Rebalancing the Cap Table37:21 Anti-embarrassment Provisions40:18 Renegotiating the SHA and the Articles42:58 The Reasons to Start Preparing Early47:15 LennonLegal.com48:03 Final Thoughts and Key TakeawaysGet in touch with Gretchen Lennon at gretchen@lennonlegal.com to get legal advice tailored to your situation.Find our more about Evgeny's work as a CEO coach at www.evgeny.coach.Startup CEO Succession: a Founder's Guide to Leadership Transition is out now. Get your copy on Amazon. 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

Jonathan Lerner of Smedvig Ventures discusses the critical journey from founder to CEO: the challenges of this transition, the importance of early and open conversations about CEO succession, and how speaking more openly about CEO succession can help founders be happier and help investors enjoy higher returns.“It's a really big transition from founder to CEO. We need to talk about it more as an industry.  It is not a failure to not make it; it is merely, I guess, a statement of what you are great at and what you're not great at.Once we get to that point, we'll have far happier founders and investors;  we'll have more successful businesses as well, so that the returns will ultimately be better.”This podcast is hosted by Evgeny Shadchnev, an ex-CEO, author and founder coach specialising in CEO succession. Find out more about his work at evgeny.coach.Startup CEO Succession: a Founder's Guide to Leadership Transition is out now. Get your copy on Amazon.00:00 Introduction01:35 What got you here won't get you there03:23 CEO transition from VC's point of view  10:11 When to start delegating15:52 Backing founders, not evaluating CEOs18:10 When is a startup ready for a new CEO?21:11 Founders starting a succession conversation27:25 Investors starting a succession conversation29:49 Legal aspects of asking a CEO to leave32:30 Wisdom of discussing it early36:32 Transitioning to a non-CEO role40:59 Rebalancing the cap table43:09 Aligning a fundraise with a CEO succession48:54 Internal vs external candidates50:59 "It always happens too late"52:31 Raising it at the board level53:51 Balancing different responsibilities56:18 The cost of not being close to the business59:06 What helps founders grow into CEOs01:02:18 Shifting the conversation as a community01:04:17 The importance of building trust01:06:38 Summary of the conversation 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

Tom Robins shares the story of taking over from Adam Fudakowski, A founder of Switchee, as the CEO.We discuss the process of getting the first job as CEO, the differences between a founder's skill set and an operator's skill set, the dynamics of the relationship between a new CEO and the previous CEO if they stay on the team, and the board's role in the process.00:00 Introduction01:32 Joining Switchee05:15 Founders vs CEOs12:36 Landing the first CEO job20:09 Taking an interim title22:37 A 3-month sabbatical for the CEO29:12 Earning the team's trust32:45 Renegotiating the relationship with the founder39:07 Building bridges with the board42:43 Reshaping the senior team44:38 Advice for aspiring CEOs47:24 What founder CEOs get wrong53:08 Episode summaryEvgeny Shadchnev is a founder coach who works with entrepreneurs and CEOs to ensure smooth CEO successions. Find out more about his work at www.evgeny.coach.Startup CEO Succession: a Founder's Guide to Leadership Transition is out now. Find it on Amazon in hardcover, paperback and Kindle formats. 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