The world of early stage companies is an enticing one. There are dreams about being employee number 10 at the next Google; of being the first product hire at Anthropic. These are dreams that come true in real life, for real people!
In reality, what mostly happens is that a group of people get together and slog away at something that ends up not working. The numbers around this are irrefutable. 50% of startups fail in the first five years, two-thirds wash out in 10, and 75% of early stage companies fail to return investor capital. There is another reality that starts to surface when you look at a different number: average tenure of product leaders at early stage companies.
The average product leader lasts sub-18-months. We know that working at a startup is difficult, but why are product leaders getting chewed up and spit out at an alarming rate, quantitatively much faster than leaders of other functions?
In 2025, I had a conversation with yet another product leader who had crashed out of a startup that had just accepted its first series A investment. He had been with the company 6 months, it was his first product leader position at a startup, but not his first rodeo in leadership. He had serious product chops, could point to major wins in terms of growth and scaling at other organizations, and was generally great at what he did. After this last gig, he was demoralized, frustrated, but mostly confused. What had happened?
As I listened to him speak, I started chuckling - he asked why.
“Because this sounds eerily similar to other stories I’ve heard, and stories that I’ve lived.” This is the story that no one talks about in public, the story that you have to find out through experience, whisper networks, coffee chats, and back-channels. It was this conversation that spurred me to do something I’ve been thinking about doing for five years, which is to dig into these stories and make sense of what is actually going on. So I started doing what any good product person does: research.
To date, I’ve interviewed 30 product leaders. I wasn’t looking for product leaders who had a negative experience, but rather I just recruited “product leaders who have had at least one job at an early stage company.” What came out of these conversations was certainly worth sharing.
The first key structure that came out - and it shouldn’t surprise anyone - is that companies exist on a spectrum. There is a tiny, gilded layer of “Rockets”, which are companies that have clear product/market fit, great vision, excellent execution, and are flying up and to the right. These don’t all look like Anthropic - they aren’t all headed for unicorn status - but they are working, and working well. You will still work extremely hard, and these companies will rule your life, but it’s incredibly fun to work at this type of place.
The next layer of company is the widest, and encompasses a vast array. I call this section the “Messy Middle.” People are messy, building a company is hard, and there are a lot of pitfalls that are easy to fall into. Things trend to the dysfunctional, and it is possible to get a case of the Sunday Scaries, but these organizations are typically workable, and if the company’s context is a good match for the product leader’s style and skillset, they can still have a meaningful impact.
The final layer is luckily a minority, but are far too numerous to let your guard down. These are organizations that I refer to as the “Toxic Wastelands”, because you just straight up don’t want to touch them. These are the orgs that I wanted to suss out, dig into, and figure out how to identify.
These are organizations that take bites out of product leaders, chew them up, and spit them out. They are damaging to confidence, and to careers. If you wash out of one of these organizations, you find that they are difficult to explain when interviewing, as you can rarely point to any value you created. The best narrative you can often come up with is what you’ve learned, or what you would NOT do in the future. That’s useful, but doesn’t always make you the strongest candidate against others that can point to scaling and growth.
Of the 30 product leaders I spoke to, 100% - in other words, all of them - had at least one experience at a Toxic Wasteland company. They are much more common than we would like.
It’s been a year since I started writing up my findings. I’ve given a few talks, and without fail after each one, people come up to me and tell me that they thought it was just them. They assumed they had failed; that they had screwed up, or had come to believe that they simply couldn’t cut the mustard. These are experienced product leaders with real track records, and one startup role was enough to shake their confidence and stall their careers.
That’s why this matters. When a product leader exits a startup, they rarely get an honest account of what happened.
They’re told they weren’t the right “fit”, and they’re left carrying the blame for problems that were often structural: an unclear mandate, a founder who couldn’t let go of product or “vision”, or a role that was never set up to succeed. Without understanding those dynamics, they go into their next role second-guessing their own judgment, or they avoid startups altogether. And the startups lose too, because the same pattern plays out again with their next hire.
Not every startup is a bad place for a product leader. Some are chaotic, underfunded, and moving too fast, but those can still be great places to do meaningful work. Some organizations, however, are set up in a way that almost guarantees a product leader will fail, no matter how skilled they are.
The good news is that the warning signs are usually visible before you sign the offer, if you know what to look for. If you’re considering a role at a startup, the first thing I want to impress upon you is this: go in with the mindset that YOU are interviewing THEM, and don’t accept an offer until you’re confident you have answers to your questions. What follows is a high-level summary of what to look for while you’re interviewing. I go deeper into each of these on my Substack.
The founder sets the tone for everything. A dysfunctional founder cascades through the organization: agreeing becomes safer than being right, and decisions follow loyalty rather than evidence. Hypergrowth and messy middle companies are hard, but the mess is a problem a good product leader can help solve. Both are workable. The toxic wasteland is different. The mess comes from the leadership, the same failures repeat with each new hire, and no amount of skill will “fix” it.
Ask questions like:
“Tell me about a time someone on your leadership team changed your mind. What did they do?”
“What’s a product decision you made that turned out to be wrong? How did you find out?”
Many founders hire a VP of Product or CPO because an investor told them to. That doesn’t mean they know what a product leader does, or what they’ll need to give up to make room for one. A simple diagnostic question: “Has anyone here worked with a VP of Product or CPO before?”
If the answer is mostly, “No”, you’ll be defining the role while doing it, and explaining your value to people with no reference point. If the answer is, “Yes”, ask about their process, their impact and perhaps most importantly, why they left.
When nobody understands product, people fill the gap with their own assumptions. There’s roughly a 50/50 chance you’ll be seen as stepping on someone’s territory. Someone was doing product work before you arrived: the CTO, the head of sales, the founder. They didn’t ask for you, and now you’re taking over something they considered theirs. People resist your decisions, go around you, or go over you to the founder. Together, these leave you isolated: accountable for outcomes without the authority to influence them.
In interviews, ask each leader what they expect product to own. If their answers contradict each other, you’re walking into a turf war.
In a toxic environment, there’s no good move. If you just agree with the founder and then things fail, you “should have” objected. Push back and you’re being obstructionist, or moving too slowly. When every outcome ends with the product leader taking the blame, the role isn’t leadership. It’s a punching bag.
Focus on whether leadership has worked with product leaders in the past. If the answer is NO, that’s something to dig into. If the answer is Yes, then ask what happened to the last person in your role. If every story ends with the previous leader not being good enough, you’re likely the next expendable chapter.
This one was the most delicate practice utilized, but highly effective for those who did it well. From my interviews nearly ⅓ felt that they gained more confidence about accepting a role after speaking with someone who had worked with a founder or a leader in the past. Another 3 leaders I interviewed were able to speak to individuals that gave them information that allowed them to feel confident that it was not an opportunity that they wanted to accept.
While it’s not easy to send cold DMs to strangers, if you lead with honesty and discretion, there is a good chance that they will be willing to speak with you.
On a practical level, it’s quite logical: they check your references, so you should check theirs. Find people who have worked for them - especially those who left, or weren’t a “fit”. Ask them what it was like to disagree, how decisions got made, and why they ultimately parted ways. These conversations are worth their weight in gold. They’ll tell you what no interview will, and could save you years of wondering what you did wrong.
None of this is meant to dissuade you from exploring leadership roles at early stage companies. The right environment depends on what kind of leader you are: what motivates you, what feels like growth, and what crushes you. Some product leaders are fixers and operators with thick skin who thrive on a challenge that would flatten someone else. If that’s you, a messy situation might be exactly the right fit. The key is seeing the challenge for what it is before you say yes.
One of the most hopeful findings from my research is this: among all the leaders who stayed in early stage companies after a bad experience, every one of them went on to have a great experience, and some had several.
Why? Because they learned to trust their gut, and their gut had been trained by experience. They knew the red flags, they asked the hard questions, they did their homework, and they were willing to walk away from anything that wasn’t a full-throated, “YES”.
That’s a skill you have to develop. It takes time to learn that there is always another job, and that the best way to land the roles that are right for you is to turn down the ones that aren’t.
I think back to the product leader I spoke with in 2025, sitting across from me, demoralized and confused about what had gone wrong. What I wish I could have told him then is what I know now, after 30 conversations: it wasn’t just him.
It isn’t just you, either. If you’re in a tough position right now, let this be your permission to stop blaming yourself for problems that a whole organization built.
--
What I’ve shared here is a summary of my findings. For deeper dives into each of these warning signs, subscribe to my Substack: https://practicemakesproduct.substack.com/
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The world of early stage companies is an enticing one. There are dreams about being employee number 10 at the next Google; of being the first product hire at Anthropic. These are dreams that come true in real life, for real people!
In reality, what mostly happens is that a group of people get together and slog away at something that ends up not working. The numbers around this are irrefutable. 50% of startups fail in the first five years, two-thirds wash out in 10, and 75% of early stage companies fail to return investor capital. There is another reality that starts to surface when you look at a different number: average tenure of product leaders at early stage companies.
The average product leader lasts sub-18-months. We know that working at a startup is difficult, but why are product leaders getting chewed up and spit out at an alarming rate, quantitatively much faster than leaders of other functions?
In 2025, I had a conversation with yet another product leader who had crashed out of a startup that had just accepted its first series A investment. He had been with the company 6 months, it was his first product leader position at a startup, but not his first rodeo in leadership. He had serious product chops, could point to major wins in terms of growth and scaling at other organizations, and was generally great at what he did. After this last gig, he was demoralized, frustrated, but mostly confused. What had happened?
As I listened to him speak, I started chuckling - he asked why.
“Because this sounds eerily similar to other stories I’ve heard, and stories that I’ve lived.” This is the story that no one talks about in public, the story that you have to find out through experience, whisper networks, coffee chats, and back-channels. It was this conversation that spurred me to do something I’ve been thinking about doing for five years, which is to dig into these stories and make sense of what is actually going on. So I started doing what any good product person does: research.
To date, I’ve interviewed 30 product leaders. I wasn’t looking for product leaders who had a negative experience, but rather I just recruited “product leaders who have had at least one job at an early stage company.” What came out of these conversations was certainly worth sharing.
The first key structure that came out - and it shouldn’t surprise anyone - is that companies exist on a spectrum. There is a tiny, gilded layer of “Rockets”, which are companies that have clear product/market fit, great vision, excellent execution, and are flying up and to the right. These don’t all look like Anthropic - they aren’t all headed for unicorn status - but they are working, and working well. You will still work extremely hard, and these companies will rule your life, but it’s incredibly fun to work at this type of place.
The next layer of company is the widest, and encompasses a vast array. I call this section the “Messy Middle.” People are messy, building a company is hard, and there are a lot of pitfalls that are easy to fall into. Things trend to the dysfunctional, and it is possible to get a case of the Sunday Scaries, but these organizations are typically workable, and if the company’s context is a good match for the product leader’s style and skillset, they can still have a meaningful impact.
The final layer is luckily a minority, but are far too numerous to let your guard down. These are organizations that I refer to as the “Toxic Wastelands”, because you just straight up don’t want to touch them. These are the orgs that I wanted to suss out, dig into, and figure out how to identify.
These are organizations that take bites out of product leaders, chew them up, and spit them out. They are damaging to confidence, and to careers. If you wash out of one of these organizations, you find that they are difficult to explain when interviewing, as you can rarely point to any value you created. The best narrative you can often come up with is what you’ve learned, or what you would NOT do in the future. That’s useful, but doesn’t always make you the strongest candidate against others that can point to scaling and growth.
Of the 30 product leaders I spoke to, 100% - in other words, all of them - had at least one experience at a Toxic Wasteland company. They are much more common than we would like.
It’s been a year since I started writing up my findings. I’ve given a few talks, and without fail after each one, people come up to me and tell me that they thought it was just them. They assumed they had failed; that they had screwed up, or had come to believe that they simply couldn’t cut the mustard. These are experienced product leaders with real track records, and one startup role was enough to shake their confidence and stall their careers.
That’s why this matters. When a product leader exits a startup, they rarely get an honest account of what happened.
They’re told they weren’t the right “fit”, and they’re left carrying the blame for problems that were often structural: an unclear mandate, a founder who couldn’t let go of product or “vision”, or a role that was never set up to succeed. Without understanding those dynamics, they go into their next role second-guessing their own judgment, or they avoid startups altogether. And the startups lose too, because the same pattern plays out again with their next hire.
Not every startup is a bad place for a product leader. Some are chaotic, underfunded, and moving too fast, but those can still be great places to do meaningful work. Some organizations, however, are set up in a way that almost guarantees a product leader will fail, no matter how skilled they are.
The good news is that the warning signs are usually visible before you sign the offer, if you know what to look for. If you’re considering a role at a startup, the first thing I want to impress upon you is this: go in with the mindset that YOU are interviewing THEM, and don’t accept an offer until you’re confident you have answers to your questions. What follows is a high-level summary of what to look for while you’re interviewing. I go deeper into each of these on my Substack.
The founder sets the tone for everything. A dysfunctional founder cascades through the organization: agreeing becomes safer than being right, and decisions follow loyalty rather than evidence. Hypergrowth and messy middle companies are hard, but the mess is a problem a good product leader can help solve. Both are workable. The toxic wasteland is different. The mess comes from the leadership, the same failures repeat with each new hire, and no amount of skill will “fix” it.
Ask questions like:
“Tell me about a time someone on your leadership team changed your mind. What did they do?”
“What’s a product decision you made that turned out to be wrong? How did you find out?”
Many founders hire a VP of Product or CPO because an investor told them to. That doesn’t mean they know what a product leader does, or what they’ll need to give up to make room for one. A simple diagnostic question: “Has anyone here worked with a VP of Product or CPO before?”
If the answer is mostly, “No”, you’ll be defining the role while doing it, and explaining your value to people with no reference point. If the answer is, “Yes”, ask about their process, their impact and perhaps most importantly, why they left.
When nobody understands product, people fill the gap with their own assumptions. There’s roughly a 50/50 chance you’ll be seen as stepping on someone’s territory. Someone was doing product work before you arrived: the CTO, the head of sales, the founder. They didn’t ask for you, and now you’re taking over something they considered theirs. People resist your decisions, go around you, or go over you to the founder. Together, these leave you isolated: accountable for outcomes without the authority to influence them.
In interviews, ask each leader what they expect product to own. If their answers contradict each other, you’re walking into a turf war.
In a toxic environment, there’s no good move. If you just agree with the founder and then things fail, you “should have” objected. Push back and you’re being obstructionist, or moving too slowly. When every outcome ends with the product leader taking the blame, the role isn’t leadership. It’s a punching bag.
Focus on whether leadership has worked with product leaders in the past. If the answer is NO, that’s something to dig into. If the answer is Yes, then ask what happened to the last person in your role. If every story ends with the previous leader not being good enough, you’re likely the next expendable chapter.
This one was the most delicate practice utilized, but highly effective for those who did it well. From my interviews nearly ⅓ felt that they gained more confidence about accepting a role after speaking with someone who had worked with a founder or a leader in the past. Another 3 leaders I interviewed were able to speak to individuals that gave them information that allowed them to feel confident that it was not an opportunity that they wanted to accept.
While it’s not easy to send cold DMs to strangers, if you lead with honesty and discretion, there is a good chance that they will be willing to speak with you.
On a practical level, it’s quite logical: they check your references, so you should check theirs. Find people who have worked for them - especially those who left, or weren’t a “fit”. Ask them what it was like to disagree, how decisions got made, and why they ultimately parted ways. These conversations are worth their weight in gold. They’ll tell you what no interview will, and could save you years of wondering what you did wrong.
None of this is meant to dissuade you from exploring leadership roles at early stage companies. The right environment depends on what kind of leader you are: what motivates you, what feels like growth, and what crushes you. Some product leaders are fixers and operators with thick skin who thrive on a challenge that would flatten someone else. If that’s you, a messy situation might be exactly the right fit. The key is seeing the challenge for what it is before you say yes.
One of the most hopeful findings from my research is this: among all the leaders who stayed in early stage companies after a bad experience, every one of them went on to have a great experience, and some had several.
Why? Because they learned to trust their gut, and their gut had been trained by experience. They knew the red flags, they asked the hard questions, they did their homework, and they were willing to walk away from anything that wasn’t a full-throated, “YES”.
That’s a skill you have to develop. It takes time to learn that there is always another job, and that the best way to land the roles that are right for you is to turn down the ones that aren’t.
I think back to the product leader I spoke with in 2025, sitting across from me, demoralized and confused about what had gone wrong. What I wish I could have told him then is what I know now, after 30 conversations: it wasn’t just him.
It isn’t just you, either. If you’re in a tough position right now, let this be your permission to stop blaming yourself for problems that a whole organization built.
--
What I’ve shared here is a summary of my findings. For deeper dives into each of these warning signs, subscribe to my Substack: https://practicemakesproduct.substack.com/
Toronto Product Management Association (TPMA) is a community focused on development, growth and networking of Product professionals in the Greater Toronto Area.
