A particular reason I love this story is that not only it went very well, but it wasn’t by accident. Nate prepared very carefully for it, thinking it through and taking his time to plan it — without either rushing or procrastinating.

Another reason this story is of particular interest to me is that Nate didn’t have to step down, as he explains in the episode. He built a business he’s proud of — profitable, growing, stable, with a solid PMF — but also recognised that for a number of reasons he didn’t want to lead it going forward. It’s wonderful to witness someone operating with this level of self-awareness.

If you’re contemplating your own CEO transition, check out his story. It’s both inspiration and a roadmap. Enjoy the episode!

His advice?

The first thing is to try [getting] involved with companies where you're not going to need to transition the CEO.

Why? CEO transitions are very risky at the best of times.

Whenever you hire a new chief exec into a company, maybe the chances of it working are, like, 50% to 60%.

Yet, sometimes, the CEO change is exactly the right thing to do, as was the case at Makers.

In this episode, Nic and I discuss the do’s and don’ts of CEO succession that he learned by participating in several leadership transitions in his portfolio, including, of course, my own startup, Makers.

Enjoy the conversation!

Timestamps

(Clickable on YouTube)

00:00 Introduction

02:14 How Not To Force Out a CEO

09:12 The Risks Of Removing a CEO

10:52 Selecting the Right Successor

14:59 We'll Invest If You Step Down

19:58 CEO Transition at Makers

27:05 Key Factors for a Successful Transition

32:00 How To Start Discussing a CEO Succession

39:42 CEO Performance vs Company Performance

41:25 Advice for Founders and Investors

49:01 Final Reflections

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 Introduction

02:32 Over-Identification with Work

07:23 True Self and False Self

15:00 This Suffering is Avoidable

27:28 "I'm 61. It took 60 years, you know?"

33:59 Wisdom Practices

40:04 Love, Safety and Belonging

48:22 Letting Go vs Giving Up

53:10 Standing Still When Your Hair Is On Fire

56:14 Challenges That Are Not Ours To Face

01:00:25 Successful CEO Transitions

01:09:07 Final Reflections

1. Unconditionally Human (essays on Sundays) about AI-first startups, coaching, etc.

2. Startup CEO Succession (this podcast).

You can (un)subscribe to them individually.

While AI is all the hype today, Matt Colebourne founded and sold an AI startup 30 years ago. Since then, he put five further exits under his belt as a professional CEO who’s often brought in to turn around struggling firms or scale promising ones.

Needless to say, as both a founder CEO and a professional CEO, Matt has a lot to say about CEO successions. One of the key lessons? Founder CEOs don’t have to rush to leave. There’s a false narrative among some entrepreneurs but especially investors that once the company starts to scale, it’s time to bring in professional management.

The truth is, no CEO knows it all or has all the required skills. However, as long as they are willing to surround themselves with even more capable people and get out of the way, they have a chance of focusing on what they’re uniquely good at.

I’m grateful to Matt for sharing his hard-earned wisdom from his 30-year career (that’s not nearly over yet!).

Enjoy the conversation!

Timestamps

(Clickable on YouTube)

00:00 Introduction

01:53 Matt Colebourne's Career Journey

07:07 Replacing Founder CEO at Searchmetrics

17:06 Stepping Down vs Compensating for Weaknesses

22:36 Transforming Searchmetrics

26:52 Product Features vs Customer Needs

32:47 Turning around Qwist Group

39:34 Advice for Founders, CEOs and Investors

53:53 Final Reflections

1. Unconditionally Human (essays on Sundays) about AI-first startups, coaching, etc.

2. Startup CEO Succession (this podcast).

You can (un)subscribe to them individually.

Most CEOs have experience with companies of similar size: some people are great at leading startups and others at leading multinationals. , however, has experience in top roles across small, mid-sized and large companies, across different countries and markets.

In our conversation today, we discuss what it’s like to lead a business at different levels of scale: what parts of the skillset are similar, and what parts are different. We also discuss the importance of soft skills. It’s ironic that we call them soft skills, given they are often harder to acquire and use than so-called hard skills.

Judit writes a Substack , has a website and is on LinkedIn.

Enjoy the conversation.

Timestamps

(Clickable on Youtube)

00:00 Introduction

01:05 Judit's Professional Background

09:32 Fixed vs Beginner's Mindset

15:01 CEO: Same Title, Three Different Jobs

18:17 Role of a COO

24:03 The Job of a CEO

34:10 The Importance of Soft Skills

44:11 The Importance of Listening

47:17 Building Soft Skills in a Hybrid World

58:34 Final Reflections

In our conversation today, Dhruv recalls the trials and tribulations of building Factmata, constantly fundraising while executing several pivots trying to find a solid PMF, before hiring another CEO with a mandate to sell the business.

Building a startup is hard. It’s especially hard as a single founder who must both run the business and raise the necessary funding. Yet, Dhruv built the business, found the right CEO to take over from him and sell the business. Today, Dhruv is an Applied AI Product Manager at Uber.

In our conversation today we discuss what it was like for him to go on this journey from an idea to a CEO transition to an exit, before moving to a career in the corporate world.

Timestamps

(Clickable on YouTube)

00:00 Introduction

01:35 Factmata's Early Days

05:14 Equity for Early Team Members

10:45 Fundraising for a Pivot

20:15 Fundraising as a Solo Founder

24:21 Delegating to the Team

30:41 Constant Fundraising

36:59 Finding a Replacement CEO

38:56 The Second Attempt to Hire a CEO

44:05 Next Steps After Factmata

46:16 Preparing for Acquisition

52:54 Post-Exit Reflections and Career Transition

01:02:42 Final Reflections

But he had energy for more. In 2016 Neal founded TPXimpact that he took public and grew to £90M in revenue in only five years, including 16 acquisitions along the way.

Yet, after five years of hyper-growth and million-profit months, his chair asked him to step down as a CEO. In Neal’s words,

“ I came away shell shocked, came home afterwards, sat at home thinking, Oh, wow. I'm not going to be running this thing that I created.”

In this episode, Neal and I discuss his entrepreneurial journey, the reasons his board suggested he steps down despite achieving incredible growth at TPXimpact and what he would have done differently with a benefit of hindsight.

Timestamps

(Clickable on Youtube)

00:00 Introduction

01:29 Neal Gandhi's Entrepreneurial Journey

05:36 Stepping Down as CEO

09:17 Navigating the CEO Transition

14:35 Running a Business in Hyper-Growth Mode

16:57 "Honestly, It Was a Surprise"

22:49 Choosing a Successor

25:54 Do CEOs Have to Step Down?

28:52 What Could Have Gone Differently?

38:47 Transition to New Leadership

41:50 Next Steps

45:18 Advice for Founders and CEOs

50:14 Advice for Boards

55:28 Public vs. Private Company CEO Succession

58:48 Final Reflections

But when we spoke privately a year ago, James didn’t know how the year would unfold. Managing multiple challenges on personal and professional fronts, James made two key choices.

First, he appointed his successor, making sure the company can run without him as a CEO. Second, he took a two-month sabbatical to recharge and recover. He did it not because it was easy to leave the business, but despite all the pressure of the moment.

Then, James came back to London well-rested and successfully sold the business to MixCloud in the following few months. And this week, he’s starting his new role with one of the hottest AI companies in the world.

Listen to the episode for a complete story!

Timestamps

(Clickable on YouTube).

00:00 Introduction

02:13 The Journey of Encore

05:16 Startup Challenges and Burnout

07:03 The Sabbatical Decision

12:13 Preparing for Succession

18:43 Returning to Encore

23:52 Meditation and Mindfulness

32:43 The Power of Running

35:10 Choosing to Step Away from Encore

40:43 Choosing the Next Step

44:51 Joining Eleven Labs

51:40 Advice for Founders

58:14 Final Reflections

A reminder: This newsletter has two sections:

• Unconditionally Human (essays on AI, startups, etc)

• Startup CEO Succession (the podcast)

You can (un)subscribe to them individually.

By virtue of her work in executive search, Maria has seen more CEO transitions from the inside than most investors. In this conversation, she shares what works and what doesn’t during the delicate process of CEO change in a startup.

Enjoy the conversation!

Timestamps

(Clickable on YouTube)

00:00 Introduction

01:32 About Erevena

04:15 The Complexities of CEO Succession in Venture-Backed Startups

08:50 Replacing vs Augmenting a Founder CEO

11:01 Starting the Conversation Early

16:19 The Timeline and Process for a Smooth CEO Transition

22:41 The Role of Coaches, Chairs, and Non-Execs in CEO Succession

26:17 Hire Right to Remain as CEO

33:50 The Drivers of Success of CEO Change

37:17 The Risks of Hiring with Intent to Promote to CEO

39:58 First-time CEOs vs Experienced CEOs

42:14 Insiders vs Outsiders

44:12 What Happens to Founder CEOs After They Step Down

47:36 Advice for Founders And Investors

56:38 Key Takeaways

So, Avin looks at CEO succession from three perspectives: as a VC, an angel investor, and a founder.

This makes him uncharacteristically blunt when talking about VCs:

Most investors say that [they] back exceptional teams, and I used to say this too, but I'm a bit sceptical about this on reflection. Most of the time, management teams get replaced.

You have no idea what that leadership team or that leader or that CEO or that founder has sacrificed, and you are stabbing them in the back. <…> I'm not saying you shouldn't do it, but you are still fundamentally, to some extent, betraying their trust.

What would make Avin consider stepping down as a CEO? Would he ever do it at Housekeep? Has he ever considered hiring a professional CEO?

Listen to the episode to find out.

Timestamps

(Clickable on YouTube)

00:00 Introduction

03:31 Most Founders Think They're Great

07:30 Two out of Three Times Founders Are Pushed Out

09:47 Inflection Points in Business Growth

19:04 Could Someone Run Housekeep Better?

21:51 Balancing Leadership and Personal Life

25:16 Roles of Founder and CEO at Housekeep

29:48 What Founders Bring To The Table

32:51 Why Most Founding Teams Get Replaced

36:08 Identifying Strong Founders

42:37 "I Encourage All Founders To Just Keep Going"

50:42 A Fundamental Betrayal

53:16 Final Reflections

Yet, some parts of his story are anything but stereotypical. First, he advocates for increased taxes on wealthy people like him to create a more just society. As Graham puts it, he didn’t check the rate of capital gains tax when he founded his business1.

Second, six years into the journey, Graham chose not to lead the business as CEO going forward but instead focus on his work as a CTO, working under an external, experienced CEO who turned out to be “the toughest boss” Graham ever had.

Not every founder CEO chooses to hire an experienced scale-up CEO and then stay working with them for nearly a decade, learning what it’s like to be part of a high-performing executive team. Spoiler: it wasn’t easy at all, but it was worth it.

Enjoy the conversation!

Timestamps

(Clickable on YouTube)

00:00 Introduction

01:59 Should We Tax Wealthy People More?

12:53 The Early Days of Photobox

18:18 A Merger with a Competitor

22:11 The Toughest Boss I Ever Had

29:13 Being Part of an Executive Team

30:00 Challenges That Shape Us

35:04 When To Go Fast and When To Go Slow

37:33 Advice To Own Son

41:36 Advice To Other Founder CEOs

46:26 Fresh Eyes Exercise for Leaders

51:02 Final Thoughts

As I said in the episode, it’s about our company and our transition. I might have founded the company, but Claudia took it to a new level since she took over as CEO.

Claudia joined as a chair back in 2017, but when we first met, she wasn’t looking for a chair role, and I wasn’t planning to step down as CEO. Yet, two years into her role as a chair, we started discussing the possibility of a CEO change. The company needed a different set of skills for its next stage of growth, and I was keen to move on for personal reasons.

Claudia would make a great scale-up CEO, but what were the chances? At the time, she was CEO of a different business. Plus, as an ex-partner at McKinsey with experience working at high levels of government, she had a wide choice of career options. So I had to pinch myself when I managed to persuade her to take over Makers.

In this episode, we discuss how we navigated our CEO transition, the first big crisis after she took over, and the lessons we learned from the experience.

This CEO transition was, in fact, the reason why I later wrote a book on CEO transitions (buy it on Amazon) and started working with other founders as a coach. It’s such a consequential and delicate process that it requires careful planning. Yet, very few founders and boards start planning it well in advance.

Enjoy the conversation!

Timestamps

Clickable on YouTube.

00:00 Introduction

01:47 What is Makers?

03:58 From Chairman to CEO of Makers

06:36 The Initial Conversations About Succession

11:13 The Decision to Change the CEO

18:35 Navigating the Pandemic

22:59 The Handover Process

31:12 First Crisis as the New CEO

35:11 Biggest Lessons

39:25 Final Reflections

At the start, visionaries run the show because there will be nothing to integrate unless they are successful. As the business starts to scale, though, visionaries learn that the strength of their vision can only take them so far. The growing business requires a new set of skills.

These aren’t necessarily two different people but rather two skills businesses need. Sometimes, one person can do both. In other companies, different people play these roles. It could be two co-founders, a founder and a COO or two different CEOs, as it happened at Puraffinity, a London-based advanced materials company working to remove “forever chemicals” from water.

Henrik Hagemann founded the business a decade ago based on his research at Imperial College London. Today, as the business continues to scale, it’s led by a new CEO who took over just two months ago.

In this episode, Henrik and I discuss the differences between the integrator and visionary CEO skillsets, the process that led him to decide to step down as a founder CEO, the search process that considered no fewer than 340 candidates, his next steps, and the lessons he learned during this transition.

Enjoy the conversation!

Timestamps

(Clickable on YouTube)

00:00 Introduction

01:42 About Puraffinity

04:53 Henrik's Role as Founding CEO

08:57 The Decision to Step Down as CEO

23:30 The Search for a New CEO

35:57 Inclusive Hiring and Psychometrics Tools

39:36 Zeroing in on the Successful Candidate

42:16 Handover and Onboarding

46:29 Transitioning from CEO to New Role

51:29 Transition Lessons and Next Steps

56:56 Advice to Other Founders

01:01:30 Final Thoughts

Alicia Navarro founded and led the business for over a decade before a big realisation. First, leading a startup for so long was taking its toll on her physically and emotionally. Second, the growing business needed a different set of skills.

The trigger was the sense of, “Gosh, this is not just something that's impacting the business. It's starting to impact me physically.”

I know that I'm a brilliant early-stage founder. And I think that the skills that you need to be a 0-to-1 are just very different from what it takes to get 1-to-N, and EBITDA maximisation is very much about operations, and processes, and structure, and finances, and they were not my skills.

Alicia identified an internal candidate for CEO succession and, after some discussion, persuaded the board to agree to her plan. Two years later, after Seb optimised the business to perform, it was sold.

He was really great at, “How do you optimize code? How do you streamline operations? How do you make things faster, lighter, better?” And that really played to his strengths. So that was one of the key projects he did. And then he also just really optimized the sales machine and brought in a lot of structure and rigor and process.

And as a result of that, he did a great job. He really, massively increased the profitability of the company.

Would Alicia do anything differently? Not really.

The measure of success is, “Do I have to worry about money anymore now? Not really. And did I create something that is indisputably a success? And the answer is yes.”

This is an excellent case of a 0-1 CEO and a 1-N CEO who did a great job together. They had complementary skills: Alicia built a business, a foundation for future success, and Seb optimised it and took it to a good exit.

Seb and I used to talk about this concept of sequential founders rather than parallel. So this idea of, “Wouldn't it be great that rather than two founders that start at the same time, you have founders that operate one after the other, so a zero-to-one, and then a 1-to-N and it's more like a relay.”

Enjoy the conversation!

Timestamps

(Clickable on YouTube)

00:00 Introduction

01:38 Founding Skimlinks

05:53 Deciding to Step Down as CEO

10:22 The Transition Process and Board Dynamics

15:02 Physical and Emotional Toll of Leadership

17:12 0-to-1 Founders and 1-to-N Founders

22:08 Post-CEO Work as President

23:45 Power Handover

29:02 Team Reactions and Culture Shift

30:48 Post-Transition Success

33:20 Reflecting on Leadership and Lessons Learned

37:35 Board's Role in the Transition

39:05 Life After the Exit

41:22 Advice for Founders and Future CEOs

49:46 The Importance of Succession Planning

51:32 Final Reflections

To Øyvind Reed, the CEO at the time, it felt like the moment the team had been waiting for: hockey stick growth. The team grew 5x. The revenue grew 10x. And then, soon enough, came the moment of reckoning:

Let's be real, competing against the likes of Google Meet and Microsoft Teams, when it's embedded or included in a subscription that you have to host your GSuite product or your Microsoft Teams product is borderline impossible.

In 2023, Øyvind realised that after a decade of running the business, he didn’t have the energy to take the company forward:

So I had started thinking that maybe I'm not the right person to take this into the next stage because I, I really believe in the energy that a founder needs to have.

In our conversation today, Øyvind and I discuss what it was like for him to decide to step down as a CEO, how he chose his successor and approached the conversation with the board, and what he would have done differently.

When Øyvind was still the CEO of Whereby, we had a coaching relationship. As is often the case, our agenda didn’t include anything fatigue when we started working together, but that was one of the things that our work helped Øyvind to realise:

So I started to accept internally that, and through conversations with you, actually, right, that I needed also to be able to understand that there's no wonder that I was starting to feel a bit fatigued, right?

Recently, I wrote about how I think about coaching outcomes. The things we aim for when we start working together are rarely the takeaways that stay with us as impactful or meaningful afterwards.

Enjoy the conversation!

Timestamps

(Clickable on YouTube)

00:00 Introduction

01:43 The Founding Story of Whereby

03:35 Growth During the Pandemic

09:53 The Decision to Step Down as CEO

14:55 Transitioning the Leadership

20:43 Involving the Board

30:00 Internal vs External Candidates

32:28 Executing the CEO Transition Plan

33:51 The Emotional Impact of Stepping Down

35:10 Transition Timeline

37:52 Becoming the Executive Chair

38:59 Balancing Family and Professional Life

43:28 Finding the Next Professional Step

45:54 Being a Founder CEO vs. Hired CEO

47:34 Impact on the Family

49:47 Post-Transition Reflections

56:36 Advice for Founders and Investors

01:00:51 Closing Thoughts

I love Nic Yeeles’s story of reinventing his career to become a VP of Product. Today, he’s on his third VP of Product job at Resi, so we can say the career move was a success, but there’s more to it. As an ex-CEO, in all his C-level roles, he was the right-hand man to the CEO, offering a holistic perspective on the business as a founder himself.

The transition to the first VP of Product role wasn’t straightforward. Nic explains how he had to “fake it till you make it,” swallowing books and learning fast to outperform other candidates during interviews who might have had years of experience in the product department.

This story is fun—Nic is a great storyteller—but it will also be useful to any founder looking for inspiration and advice on how to transition from founder-CEO to C-level executive at another business.

Timestamps

(Clickable on YouTube)

00:00 Introduction

02:30 Founding and Exiting Peg

04:54 Founding a Climate Impact Startup

08:16 Trying a Consulting Role

11:16 The Ex-CEO Advantage

13:42 Choosing the Next Career Step

17:47 Interviewing for a Role You Never Performed

22:51 Navigating Cultural Alignment

25:44 Power of Personal Networks

28:07 Joining Resi as a VP Product

31:12 The Challenge of Identity Shift

32:53 Working with Non-Founder C-Level Executives

35:21 The Value of Entrepreneurial Skills

37:04 The Costs of Not Starting Another Business

38:34 Choosing Startups Over Large Companies

40:39 Considering Freelance and Advisory Roles

41:53 Lessons Learned

53:34 Hiring Ex-entrepreneurs

58:03 Final Thoughts and Takeaways

Over the next few years, SaveMyExams proved to be helpful to far more people than just Jamie’s students, and it became a profitable, growing business it is today, helping countless students prepare for their exams.

From the start, Jamie wanted to have the option to step down from running the company if he chose to do so. Eventually, in 2024, he promoted his COO Constance to the CEO position, moving into a chair role himself. At that point, the company was about 80-strong, but Jamie started to prepare for the potential transition when he had only about 30 people on the team.

In our conversation, we discuss how he approached the CEO succession process as an independent business owner. This is a slightly different process compared to stepping down as CEO of a VC-backed business, negotiating it with the board. However, the key principles stay the same: it’s easier to step down if the business is doing well, it’s easier to trust an insider as a CEO candidate and it’s best not to rush the process.

And, shameless plug, I was coaching Jamie throughout the transition, as he explained in the episode:

working with you as a coach <…> was a really good way to mitigate some of those risks, you know? I think one of the things I try and do is always work with people who've been there and done that and know what great looks like. And you've not only lived that but also work with a bunch of people who've gone through that process.

Enjoy the conversation!

Timestamps

(Clickable on YouTube)

00:00 Introduction

01:46 Founding Story of SaveMyExams

03:35 The Decision to Step Down as CEO

05:57 Starting the Transition Early

09:01 Mitigating Fears and Concerns

10:59 Internal Vs External Candidates

15:15 Adjusting to the New Role as Chair

17:00 Impact on the Team and the Business

19:25 Personal Reflections and Advice for Founders

30:24 Future Plans

32:38 Conclusion and Key Takeaways

There are several reasons why La Fosse stands out from the competition. First, they achieved great financial results — nearly 500 employees, nearly £200m in revenue (archived link) — all without raising funding. Plus, they won so many awards for being a great place to work, that they built a dedicated page on their website to list them all in fine print.

What’s more, Simon chose to make La Fosse an employee-owned organisation. Despite being a sole owner, he chose to give over 50% of the equity to the team, ceding the ultimate control for the benefit of the team. This is far more generous that a 5-20% employee options pool most startups have.

Given all this success and care for the team, you might be surprised to learn that Simon is not a CEO and hasn’t been for a very long time. He promoted an internal candidate to an MD position when the company was only 40 people, having recognised that his own talents lie elsewhere.

The first CEO did an incredible job, but when the time came to find a new leader, Simon promoted someone else into the CEO role again. Looking back, both CEO transitions have been a success.

In this episode, Simon and I discuss why he wanted to build a company “like no other”, the reasons he focuses so much on treating people well and how that helped La Fosse become a great business it is today.

Enjoy the conversation!

Timestamps

(They are clickable on YouTube)

00:00 Introduction

03:08 Founding La Fosse Associates

05:40 Core Values: Co-Ownership and Care

10:24 Upholding Values During Hard Times

14:34 First CEO Transition

20:08 Navigating an Inflection Point

23:41 Second CEO Transition

27:11 Trusting Founder's Intuition

29:52 Developing a People-First Culture

31:20 Simon's Next Chapter

33:46 An Ecosystem of Support

36:21 Balancing Work and Life

40:55 Advice for Future Founders

47:44 Final Reflections and Takeaways

Yet, many founder CEOs who stepped down don’t seem to take legal aspects of this transition seriously enough. In this conversation, Gretchen Lennon from Lennon Legal and I discuss the main points that all founders considering leaving their startup should be aware of.

There are two overarching points I hope founders will take from this conversation.

One is that your board is on your side only as long as you’re the CEO. When you start negotiating stepping down, they will be on the opposite side of the table, negotiating for the company. To some founders, this comes as a surprise because the investors have always been in their corner. It’s not wrong and it’s not personal: it’s just a change of roles that founders should expect.

The other one is that there’s more complexity than many founders expect before the start thinking it through: shares, options, tax, restrictive covenants, consent rights, settlement agreement, etc. etc. Founders need to understand their legal position before starting the negotiation with the board because this will shape their negotiation strategy.

(If there’s a founder who needs to watch this episode, send them the link!)

Timestamps

(Chapters are clickable on YouTube)

00:00 Introduction

02:31 Hypothetical CEO Resignation

05:06 Unfair Dismissal

08:12 Shares,  Options and Taxes

16:36 Getting Legal and Tax Advice

18:37 Negotiating Settlement Agreements

21:59 Post-Termination Restrictions

26:42 Staying with the Business as an ex-CEO

32:16 Rebalancing the Cap Table

37:21 Anti-embarrassment Provisions

40:18 Renegotiating the SHA and the Articles

42:58 The Reasons to Start Preparing Early

47:15 LennonLegal.com

48:03 Final Thoughts and Key Takeaways

As an investor, Jonathan sees companies grow from Series A to Series B, and the evolution their founders go through on the way to taking their seat as CEO. We dive into all of this in today’s episode. I shared my own reflection on the parallels between these two journey in a separate essay last year: From founder to CEO, from Series A to Series B.

Smedvig Ventures’ website has a catchy headline: What got you here won’t get you there. The mistake founders sometimes make is doubling down on what made them successful as founders when they need to step into a CEO role.

Likewise, what helped their companies to get to Series A metrics will not help them get to Series B metrics. In order to keep making progress, both the founder and the company need to change how they operate.

We explore both perspectives and much, much more in this in-depth conversation with Jonathan.

Timestamps

(They are clickable on YouTube, but not on Substack yet, I think).

00:00 Introduction

01:35 What got you here won't get you there

03:23 CEO transition from VC's point of view

10:11 When to start delegating

15:52 Backing founders, not evaluating CEOs

18:10 When is a startup ready for a new CEO?

21:11 Founders starting a succession conversation

27:25 Investors starting a succession conversation

29:49 Legal aspects of asking a CEO to leave

32:30 Wisdom of discussing it early

36:32 Transitioning to a non-CEO role

40:59 Rebalancing the cap table

43:09 Aligning a fundraise with a CEO succession

48:54 Internal vs external candidates

50:59 "It always happens too late"

52:31 Raising it at the board level

53:51 Balancing different responsibilities

56:18 The cost of not being close to the business

59:06 What helps founders grow into CEOs

01:02:18 Shifting the conversation as a community

01:04:17 The importance of building trust

01:06:38 Summary of the conversation