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Dec 13, 2023

The Case of the Frustrated Founder

Episode Summary

Leon is a founder who wants his company to succeed but hates his job as CEO and is unsure if he’s the right person to lead the team. In this first of a two-part episode, Heidi shares how the founder role changes over time, what a founder can do to navigate that change to still love their job, and an exercise to find out the best path forward. In part two, we’ll find out what happens to Leon.

Full Transcript

HEIDI: Welcome to the Startup Solution and the Case of the Frustrated Founder. I’m Heidi Roizen from Threshold Ventures.

. . .

Up until now, I’ve always talked about specific issues and how entrepreneurs might tackle them. But what do you do when it’s not just one thing: it’s everything?

LEON: Hi Heidi. This is a weird message, and I hope we can keep it just between us for now anyway. I’m driving home from work. It’s been a brutal week. I gotta tell you, I’m just not digging my job. A lot of what I did this week I didn’t enjoy. But more importantly, I’m just not sure I’m good at it. I want to do the Silicon Valley superhero thing and power through it, but in all honesty, I want the company to be successful even more. And I’m just not sure I’m the guy to make that happen. So, when you get a chance, can we spend some time talking about this? Thanks.

. . .

HEIDI: Let’s call this entrepreneur Leon.

Leon is experiencing the unintended consequences of his startup’s success. His case is remarkably common, and it’s pretty easy to see how he got here.

When Leon first started his company, he was the chief – and only – product development person. And, of course, he was the CEO – of his one-person company.  

Time passed, and good things happened for Leon. He landed some customers, got some seed funding, and hired a couple engineers. He didn’t have as much time for product development anymore, but he was still very hands-on, even coding.

More time passed, and more good things happened. And still more things became things Leon had to do as the CEO. His days were filled with financial planning, investor meetings, people issues, and lots of other stuff he neither enjoyed nor had any prior experience doing. All these tasks left him virtually no time to work on the product – the thing he actually most loved doing.

. . .

And so, Leon woke up one day to find himself hating a job that he never would have applied for, he doesn’t enjoy doing, and to be honest, he’s not very good at either. A job he created himself!

Leon is now part of a group I like to call “Frustrated Founders” – although this can happen to anyone, not just a founder. It happens when you take on a role at a high-growth company, and as the company grows and changes, so does that role. Some people love the change and enjoy taking on the new responsibilities and challenges that arise. But for others, it turns a job they loved into a job they dread waking up to every day.  

For founders, it might even feel like a Silicon Valley taboo to even talk about this – I mean, aren’t you supposed to have the top job if you start the whole thing in the first place? I’m here to tell you that just because you’re the founder, it doesn’t mean that you also have to be the CEO. You can, of course, but you don’t have to.  

There are many reasons founders choose to also be CEOs, but as Leon is discovering, it might not lead to happiness or job satisfaction... and it might not even lead to maximizing the success of your company either.

. . .

So, instead of just buckling in for an unrewarding slog, consider thinking through how to improve your situation. That’s what I helped Leon do, and I’m going to help you do that right now, too.   

And by the way, even if you are not a CEO/Founder, this exercise can help you think through any role you have that you no longer feel good about doing.

This is a process you can do completely by yourself – no one else has to be involved or even know about it. Doing it privately, at least for now, might also help you be more honest with yourself. This process only works if you can be brutally honest without letting your concerns or your ego get in the way. 

. . .

To start, I want you to mentally step out of the role you are in and promote yourself to an imaginary executive chairman role. In this new role, you still have deep knowledge about the company, as well as tremendous insights about yourself as the founder and CEO, but you are personally detached from any operating role for now.

Next, write down the top four or five priorities that your company needs to accomplish over the next two years or so. For this part, you could of course, use what you and your team have already determined as a group, or even get input from others if you feel you need it.   

After you’ve finished that, write the job description for the perfect CEO based on what you just prioritized. If you have to raise money, you will need someone good at that. If you are going to add a lot of people, someone good at leading and managing a growing team will be important. Maybe it’s now become critical to build out a sales team. Since you’ve been doing the role yourself, you should have a pretty good idea of what a CEO job description looks like. But if you need some help with this part, I’ve listed some resources for articulating a CEO job in the show notes for this episode.

. . .

Ready to move on? OK, set all that work aside and turn your attention to yourself.  

Start by creating a list of your superpowers – the things you’re great at. Next, write a list of work-related things you’re not that good at but really want to get better at, things you believe you could master if you put time and energy into them. And finally, write a list of the things you just hate and don’t really want to do, ever. Remember, no one else ever needs to see this list but you, so be honest. And for your first pass, accept whatever answers come to mind. You can negotiate with yourself later, but for now, give yourself an honest assessment with no consideration for the implications.

The next step is the hardest one, so take a breath and remind yourself to check your ego and your biases.  

. . .

Now, look back at the job description for the CEO and grade yourself as an applicant, knowing yourself as well as you do and, of course, being honest.  

You can grade on a scale, or just do good and bad, or good, bad, willing to learn, hate this stuff, would rather bite my arm off, whatever feels right to you because this is just for you.   

It’s important to be brutally honest for two reasons. One is that you’re probably one of the biggest shareholders in your company, and so I’d hope that you’d want to give your company the best chance of being successful. You are in the CEO role in part because you grew the company under you, but remember, that doesn’t necessarily mean that you’re the best person for the job… and I’d like to think that you’d want the best CEO in the role, even if that isn’t you. 

The second reason may seem counter-intuitive, but by putting yourself through a process like this and then reconsidering what role you should play going forward based on what you learn, you’ll probably end up both happier and more successful as a result. Even if that means letting go of the top job.

. . .

Maybe you’re finding that hard to believe right now, but I’m gonna play the old-person card and tell you that I’ve seen this work over many decades for many people, including me.

I’ve made a few big career transitions, from startup cofounder and CEO to being a VP at Apple to venture capitalist and board member. Some of those shifts required some real soul searching, and hard reality checks. But I’ve always done better in my career and been a happier person when I’m leaning into each day, not dreading it. That doesn’t mean there aren’t bad days or days I have to do things I don’t like to do. I often joke that’s why they call it work, and they have to pay me to do it! And that also doesn’t mean that I only do things I already know how to do. That would be boring! But when I can spend my time doing things that align with my superpowers or challenge my desire to learn in a positive way, I’m happier, my days go by more quickly, and it turns out I accomplish more, too. And when I feel myself dragging my feet, day after day, then month after month – that’s when I know that I need to check in with myself – to see whether my role and I may no longer be meant for each other.  

And from my own past experience, sometimes that has meant not taking or not staying in the job with the fanciest title,  or the highest pay, or the biggest ego strokes.  

And I can honestly say I have no regrets when I think about the decisions I’ve made this way.

. . .

But enough about me – let’s get back to you. There’s one more thing to do to complete this process: Look back at the top priorities for the company, and now, write out a job description that sits at the highest intersection of what the company needs AND what you are good at and want to do.  

Look, this is the advantage of doing this exercise – because of your status as founder and CEO, you have the opportunity and the privilege to proactively design your own dream job, if it turns out the CEO job, isn’t it.

Now that you’ve done all this, set it all aside and take a break. This process can be exhausting and emotionally draining, so I want you to just forget about it for a day or two. After that, you can revisit it to see how you feel about your answers and see if you need to adjust anything.

. . .

Also at that point, if you feel comfortable doing so, it can be illuminating to bounce this off a trusted advisor, a family member, or a close friend. Sometimes, others who know us well see insights in this work that we don’t see ourselves. But if you aren’t comfortable opening this up to anyone else, you don’t have to. It’s totally up to you.

At some point, it’ll be time to think through the practical implications of what you’ve discovered. It might indicate that your best role is not as CEO. Or it might indicate that you do want to remain as CEO but need to address some areas with coaching or other forms of assistance. Maybe you determine that it’s time to bring on a COO. There’s no perfect, one-size-fits-all answer, but to help you think through these options, we’ll talk more about them when we return after the holidays.

In the meantime, do this exercise with an open mind, sit with it a while, and see what you learn from it. 

. . .

HEIDI: And that concludes “The Case of the Frustrated Founder.” For the record, this situation is real, but Leon is a composite. And no startups were harmed in the making of this podcast.

Thanks for listening to “The Startup Solution.” We hope you’ve enjoyed this episode, and if you have, please pass it along to someone who could use it. I’m Heidi Roizen from Threshold Ventures.

Further Reading

An interesting HBR article with some data about some big names who went through CEO transitions:  How Long Should a Founder Remain CEO

An article by James Routledge that sounds a lot like our protagonist:  Founders, you don’t have to be CEO

A related topic is burnout - here’s a compendium of what founder burnout is and what to do about it:  Founder Burnout:  Meaning, Causes, Prevention, and Cure

And finally, as promised, here are some job descriptions for the two roles we are discussing: CEO.1, CEO.2, COO.1, COO.2

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