Ready to start a startup? | Shreyas Doshi (Former PM leader at Stripe, Twitter, Google)

Nikhyl: When do you know it's the right time to take this leap of founding?

And when do you kind of suggest maybe this isn't the right time?

Shreyas: So my sense is it, it is never the perfect time, and at the same time, It is always a good time, to go found your startup, I'm usually in these situations, more interested in really thoroughly exploring the why first. So why do you want to do this? And then why do you, why do you want to do this at all?

And why do you want to do this now? Right. Uh, and what I find is that it is really worth your while, to explore the why, for a very long time. You realize it is more like a. 10 year journey, right? It is not like I'm going to do this for the next three years because you and I both know nothing comes out of like a three year horizon of founding your own company.

it is 10 years in some cases at a minimum. Like, I'm sure there'll be statistics of, well, this person exited this company in 7 years or in 5 years. Fine. It's still useful to psychologically trick yourself into thinking it is 10 years, right?

10 plus years. So, the point is, it's very straightforward. It's like, a 10 plus year journey. Does it behoove you to maybe spend a week, two weeks, a month, kind of really thinking hard about that why and trying to get the clarity around the why.

Nikhyl: if someone comes to you and says, I'm struggling to kind of find a job today. Let's take the example of, you know, I've been laid off or I'm in transition. The market's really tough. I've been trying to find a role. I can't find one. I'll just make one up.

I'll go found. And, you know, that to me is, I'll do that for a couple of years and then market will improve. And then I'll jump into the next thing. What I'm hearing from you is, first of all, this sort of short term, let's do this for a couple of years instead of looking for a job or taking a job that I'm not excited about has a pretty significant challenge associated with it, because it's an identity role.

It's a long term role, et cetera. Is it? Easier to found than it is to find a job, meaning if you're struggling to find another role is founding something that anyone should consider. Or is that a signal that if you can't find a traditional product role, you're probably not going to be a good founder.

It's an open question here.

Shreyas: a couple of different angles to explore here, right? So if you are struggling to find a role, like, I guess my first question would be, What are you looking for? What are your criteria? Cause that's what I would first question. So I would assume a high degree of competence because I kind of have to.

and then I'm interested in what are you looking for? And does that match, you know, the degree of competence, that you have and the credibility that you build? and often there's some mismatch there. if that's the case, let's correct the mismatch. Let's reset some of our very high expectations.

Yes, we are ambitious. We all tend to have very high expectations and, you know, very lofty goals. That makes sense. I personally always had very lofty goals. So I get it, but there is also the recognition of the job market right now. It's, it is very tough. It is extremely tough. so I first do want to go in that direction and explore that.

and usually we will find some mismatch. Again, assuming a high degree of competence, right? now let's assume there is no mismatch. Like, you're looking for the right thing, but you're not paying attention. finding it. and it's typically like people tell me, I managed to reach like the penultimate rounds or the final rounds and then something happens, right?

And I'm not the one who gets the role. And this has happened to me multiple times, half a dozen, dozen times, to which then I go, okay, this is likely not a competence issue. Because if it were, you would get eliminated much earlier in the process. again, assuming you're interviewing at like competent companies.

but it is likely a storytelling or a style issue. And if that is the case, uh, we've got to fix it. And if at this point you're saying, well, I'll go found the company. Well, you're going to face the same problem. Thank you. And if we do indeed detect that there might be a lot of room to improve on the storytelling front, Then we've got to fix that regardless of whether you're going to go found a company or if you want to, you know, get selected past the final rounds at some director or VP level role at high quality companies.

Nikhyl: So you're hitting on a pretty core question here, which is how much of an overlap is there between being a good PM and being a good founder? So one thing that you just noted is look, storytelling is a clear skill that we need to have as product people, particularly as we grow and your note is look, founders need to have that in, you know, in significant quantities as well, because you're not just trying to sell your upper management.

Right. Or your team, you're trying to sell potential customers, investors, future employees, et cetera. So if you're struggling with storytelling as a product person, it's hard to believe you would be able to sort of immediately be comfortable in the founding type scenarios. This storytelling is a key, key skill, and we can flip it around.

We can say some product people are very strong storytellers, and that's a perhaps a tailwind. On being successful founder, maybe identify if I was to ask you, what are the couple of other things that you would say? Boy, if you have this, this is a good signal early signal that you might enjoy or be competent and founding.

And of course, the corollary of if you don't have this, it might be worth taking the extra second to sort of decide on going forward.

Shreyas: definitely storytelling is one which we already discussed. But sometimes in my coaching conversations, I also have to help people see it is not a storytelling issue. It is a story issue, right? And it is very hard for us, you know, very ambitious, very intelligent people, uh, to admit to ourselves.

Sometimes it is a story issue, i. e. it is an issue with the content. So that is definitely like one thing that is common across being a senior product leader who's operating at the highest levels of our industry.

In kind of tier one companies that are highly competent, right? And as a founder, it's even more important because at least if you're working as part of a bigger organization, there will be others who might like supply parts of the story, right? You have a lot of supporting infrastructure, to help arrive at maybe If not optimal, at least a decent story, But when you're going and founding your own company, it's all you, so I do think that like that is another like really common element and, that involves a number of skills, right? That involves, uh, the scale of creative execution that involves the scale of like customer insight, product sense, essentially.

strategic sense, commercial sense, right? Like those are really important factors, that, uh, I think many people assume because, uh, especially in a large company context, they've had, you know, very quick progression. so it is natural when we have that like kind of very quick progression to assume that we've got the story covered, right?

That we've got the content covered. and sometimes it's kind of having to really face the facts that Well, yes, I did well at this company, but the reason I, at least part of the reason I did well, is because it was already a rocket ship, right, going at 1, 000 miles per second, and yes, I did help steer it in a better direction, I maybe helped increase its speed, but I should avoid.

sort of crediting myself for all of its velocity, right, that there were many things that happened before I even showed up on the scene, that gave this thing that momentum.

Nikhyl: what I'm hearing from you, and I think this is a key point, is sometimes our success is a product of the system that we're part of. And I think the point you're making is, look, when you've found, you start from a blank sheet of paper. And when you start from a blank sheet of paper, you are essentially creating all of the momentum.

And so that doesn't mean that if you've been a Product of success of an existing system, the sort of growth that you plugged into and saw your career move that you will be incapable of starting with a blank sheet of paper, but there's no sort of core evidence that you're going to be able to do that.

Sometimes founder types come to me and say, look, I do 0 to 1 in a late stage company. I feel like I could found just as easily externally and my argument is 0 to 1 in a. Company that has 50, 000 100, 000 employees with tons of distribution and lots of perks and great engineers that are running around the building couldn't be further from the zero where the sheet of paper is truly blank, not just one page that's intentionally left blank in the book.

Right? So I feel like there's a huge discrepancy between those that are good at creating. You know, I almost describe is you have to be able to get out on the ocean and create your own wave, not just sit on waiting for a wave to come along. And that's a very, very different skill. So you have to kind of look at your own background to see what are examples where you've actually created your own momentum.

And you felt comfortable with the blank sheet of paper, because oftentimes Yeah. People that are product managers, their mindset is they have great red pens and erasers and so what they do is they go to the whiteboard. They see what's been written by someone else, maybe a founder, and then they go in and they fill in the blanks and they see what I think this is going to be off.

And have you thought about this? But when you start with the sheet of paper, it's To begin with that's blank, the board that is empty, you're essentially armed with a black pen and your job is to write and others to critique, including your market, your customer, your investor, et cetera. And so that is the very, very different scale.

Maybe my question would be, how do you know if you've had a successful product career where you've been a successful at managing scale? How can you tell? If you might have this skill, or perhaps, how can you tell if you don't have this skill?

Shreyas: there are a few heuristics, Now, of course, before I share those heuristics. I will mention that doing this kind of exploration, self exploration is tough and it feels very scary. most of us run away from things that feel scary. It's very natural. And so it requires a pretty high degree of self discipline and actually a high regard for your own self interest to do this exploration.

again, it is more tempting to avoid doing this and saying like, Oh, let's just do it. Let me just do it.

But what you've signed up for is potentially years of pain for yourself, for people around you, right? Both, you know, people in your family and people like your co workers, people you'll hire. In your best self interest to, take a few hours, take a few days, take a few weeks, to do this on a self exploration.

Okay, so with that, here are a few signs I look for, if you are going to be successful as a founder, then those signs are actually there throughout, pretty much throughout your life, right? And certainly even in your corporate career, where you're working within a 50, 000, a hundred thousand person company, right? Uh, and so a few come to mind. Uh, first is how comfortable have you been with, uh, living with ambiguity?

And just staying in that state of ambiguity for long durations of time, while at the same time, trying to correctly, resolve that ambiguity. the founding role, whether it's for a traditional startup, or if you want to start a cash business, it involves extreme degrees of ambiguity.

And one of your job is to resolve those ambiguities. Right. And so if you are the kind of person who's felt you might have been a VP, SVP at a very famous company, you might have managed orgs of thousand plus people. But if you look back at your life and career, and if you look at moments where there was a high degree of ambiguity, and that made you extremely uncomfortable, and you were looking for someone else to resolve that ambiguity.

Usually your boss, and in some cases you are blaming, you know, some other org or some, uh, other authority figure to resolve it. That's a sign perhaps, right? Like that's a sign You're going to have a tough time, right? And like, it doesn't mean you shouldn't do it, but it's just an honest sign that like, this is something we need to work on now.

And that we have to work on now. So that's one. second is, have you found yourself being extremely compliant with the optics expectations of your org? so in early life say, when you were in school, you got good grades, surely, otherwise we wouldn't be here, you did well in school or college or whatever.

but the manner in which you did well was to reverse engineer the rubric that the teacher gave you. Right? And you did everything perfectly according to that rubric. And then you got your A or A and that perhaps there were other fellow students in your class who did not get that A. Maybe they got a B But, they actually, like, you know, deep down, that they actually knew the subject matter better.

so that's like an example going all the way up to school, back to school, but even in your corporate career, have you been, frequently looking at the ladder, whatever the career ladder is and saying, okay, for this next step in the ladder, this is what I need to do.

And so now I'm going to do exactly these things in order to get to this next level, right? But do you make it your primary focus to kind of check those boxes? Right. And yes, in order to check some of those boxes, you will strive for impact.

You will strive for great execution. You'll strive for progress. But like, what is the source of that inspiration? What is the source of that? enthusiasm you have around getting things done, if you find that you've kind of been basically trying to figure out what the rules are and then, you know, play the rules really well and play that game really well, Versus, you might still be a VP, SVP at a company, but, you know, you found yourself kind of bending some rules every once in a while, right?

You found yourself fixating on the core impact, the business impact, and you found yourself fixating on, you know, progress, right? and perhaps you had some disappointments along the way on the career front, where like, maybe you did not get promoted, uh, even though you should have, because you did not fulfill some optics requirements, like you did not check two of the seven boxes in your career ladder.

So the. The promo committee came back and your boss told you, sorry, you didn't check these two boxes in the last year, so we decided not to promote you, and in that case, surely you were disappointed because you, we are all human, so surely you were disappointed, but that did not change what you did for the next year,

Nikhyl: Yeah, I love the 2 points. I love these 2 points. So I want to make sure we go back through them because I think these are the 2 key ones that we've surfaced so far. So I think 1 is thriving in ambiguity. I think that part of the reason why I think you're saying that is when you found you are constantly dealing with not only ambiguity, but making progress in a world filled with ambiguity in a world where feedback is relatively weak, where you're constantly looking at seven different directions. But most importantly, you have to decide you have to move forward in one step or another, and that some people find ambiguity to be an incredibly fulfilling and enjoyable part of both their life as well as their.

Their career, they think back and say, even when they storytell, well, I was faced with all these different directions. We went one direction. It didn't always work out. That piece, I think, resonates. If, on the other hand, you look back and think all of ambiguity is something to avoid, something to remove, something to obsolete, I think your point is that that might lend itself to a well structured environment, but it is a big signal that founding is going to take you into a place of anxiety.

I think the second point, Is very key when you think about this question, and I hear this all the time, and I hear that. Hey, I'm thinking about founding, but I'm waiting to get promoted. That's another that's another signal where there's more to that question than than than what you alluded to. But the concept of, working and mastering a system where the system is a set of rules.

Governed by an institution, in this case, an employer, or perhaps a university, et cetera, is very foreign to the blank sheet of paper, greenfield exercise of founding, where not only is there lots of direction of ambiguity, but there is no natural North star. It's not entirely clear what your objective function is.

So I think the thing that a founder that has this sort of understanding of, well, what's the. What's this system that I need to master? Well, the system is like growth or find a product that has product market fit. You know, these are not the easiest things to reverse engineer using your terminology. And so I think the combination of comfort and ambiguity and comfort in a, non-governed system, I think, are the two things that I think really resonate to me as almost not just like being able to succeed, but actually enjoying thriving.

This is your point around. I know what rules exist for me to move forward in this system. I refuse to do it because I'm governed by something maybe more internal. That is the sort of thing I'm hearing that really sends you in your own path and makes you comfortable in the founding role.

Shreyas: And Nikhil, I, a couple of thoughts I have around this is like, if you do find yourself in that sort of situation, Where it's like, yeah, if I'm being honest, I've been sort of like relying on the rules and structure, that were set up by someone else, and I am a great, implementer of those rules.

I'm a great executor of those rules, that is my strength and say you do want to be in a startup environment. Well, there are other options available to you besides just like, Oh, I'm going to go found my own company. maybe like if you want, if you still want to try a high risk path, go a startup.

Right. Where they need. That they need that structure, right? And yes, you may or may not have the founder title, but you might still be employee 10 employee 50 employee 60 you know, a senior employee at that, where you are the one who's kind of responsible, for doing this, it's better to identify that superpower of yours, right?

Because in many of, with many of these folks, this is literally their superpower, which is what made them get to, you know, these very high levels and helps them operate at these very high levels. So it's better to work In alignment with that superpower while still scratching that startup itch, if you want, if you go down the path of like, okay, I want to found the startup because like, you know, somebody I went to grad school with did it and they just exited their company for 5 billion.

Right? Like, and like, you know, I was smarter than them or I had better grades than them. So, like, you know, I should do it. What am I doing with my life? Right? Like, those, I find, are not good reasons to do it. And I find that a lot of people that end up, doing these things based on, you know, Essentially those kinds of stimuli, like they just end up not being happy, right?

Like doing it. look, founding a startup is hard. Anyway, running a startup, running any kind of business is hard anyway. Uh, why make it on yourself? Because now you're working like almost in, direct opposition to what your superpowers are.

Nikhyl: Yeah. I mean, there's a few things that come to mind as you were, you were talking. I mean, I think one is that we can also flip this around. I mean, one of the implications is. People that tend to have this type of agency, people that tend to thrive in ambiguity, people that tend to maybe slightly be allergic to well structured systems that are very heavily optics based, you know, may not perform at the highest level in the world.

In the more traditional product management environment, and yet might be outstanding founders, or maybe the flip side is you and I have worked for companies where we've ingested founders through M& A through acquisition, and many of them start as. Product managers because nobody knows what to do with these founder types and we put them in product management and they do like average jobs and it's always puzzling because you're like, wow, this person was an exceptional founder built something from scratch that was amazing and they struggled to be a product manager and it's for a lot of the reasons you mentioned where They didn't understand how to put the system or the infrastructure or the needs around collaboration in exchange to having your own ideas, driving quickly, moving fast, et cetera, which are harder to do when you have more to protect.

So my note here is you can flip it around. You can say that there's. People that are listening to this that might be feeling like there may be a slight imposter as a product manager, and in fact, they've sort of realized that they're not actually going to be all aligned in their superpower as a PM, but they may have been telling themselves this whole time.

I'm just not doing enough. At a product manager and now what we're essentially saying is, look, if you have some of these characteristics that we're, we're signaling, you might actually be far more successful as a founder where you can live in ambiguity and have a lot more kind of freedom and a lot more agency.

And so I do think that it's rare to find someone who's an exceptional executive and also an exceptional founder, like the two feel like they're almost slightly divergent skills. Particularly as you advance in career.

Shreyas: On the flip side, sometimes I'm talking to somebody who has all of those core skills, right? Like they have that creativity, they have that high agency, they have, you know, very unique customer insight. you know, it's clear that at some point they want to start a company.

It's usually when I talk to them, Oh, it's a year out. Right. Like it's a year out for personal reasons, whatever reasons, so now, uh, the question gets posed by this like highly talented person who has great potential as a founder.

that like, okay, so what should I do for the next year? when I ask them, like, what their kind of default plan is, I usually hear a some, some version of a story that goes like this, okay, so in a year, 18 months, two years, I want to start my own company. I'm currently director level.

And what I want to do is I want to get to that next level. And so then we, we get into the depths of like, okay, so why VP?

is it just because it's there, or is there some other reason, and sometimes, uh, or actually more than half the times, I hear some narrative that goes like this, again, Shreyas, like, we're very clear, you know, Sort of year plus down the road, I'm going to be starting my startup, In order to have a good shot at it, I feel like I need to get to VP and that's because then I'll be managing a bigger org, potentially, I'll be showing VP level scope when I go raise money from VCs, and it will really help me improve, uh, this kind of management ability, leadership ability. Which clearly is very important, uh, is going to be very important when I, uh, begin my job as founder CEO, that seems very logical, except then I have to, ask them questions such as, what is the main thing you need to get right in the first one, two, three years, and it takes some time to get to like clarity around that answer. But of course the right answer is, well, we need to hit some version of product market fit, something as they get to that realization, I asked them, okay, so it, would it make sense then for you to maximize your odds of success that you hit PMF.

And of course they respond. Yes, that makes sense. So then my next question is what is the main skill that will maximize your odds of getting to PMF in your startup?

And the right answer is not managing a large org. And it's not even improving my management ability, right? Or improving my skills as a leader. Right? It's not even necessarily that I need to be a, at scale leader, right? It's none of that. It's not even how well you manage your VCs and stakeholders, it is essentially product insight, product sense, right? Uh, customer insight. That is what you really need, right? And and then what happens after You hit that resonance with your product. Yes. Now you will face some scaling challenges and other challenges, but those are good challenges to have that 90 percent of startups never have.

Right. So why are we trying to optimize for a post PMF your org is scaling as a startup? Like, why are we trying to optimize for that? When that is not the main point of failure for startups, right? So if you're going to use this one year, these 18 months wisely. Perhaps actually it might make sense for you, your director right now, perhaps it might make sense for you to do a GPM level role, right?

Like something that really exercises your product sense, your product insight, and customer insight and creativity, rather than trying to deal with building a skill set around managing a very large org.

Nikhyl: I mean, I'd go one step further. I mean, this is such a great example. I think that I would say that, as opposed to chasing promotion or level, Joining a startup so that you don't have to take the risk on yourself all in one time might be a better model. And so then the theory that then you ask your person is well, if you're a director now, and you're 12 to 18 months away, for whatever reason, how do you know that you're just not scared or emotional about the leap of faith?

How do you know that you're just sort of overly intellectualizing the decision not to found the primary concern that people have around founding and why it's perpetually one to two years away is because they can't see themselves making such a jarring change. From a structured, well compensated role to a fully ambiguous, fully uncompensated or mostly uncompensated role.

And the way to test it is to say, well, if founding in and of itself is too big of a leap because you don't have the team or you don't have the idea yet, go learn on someone else's dime. Perhaps the economics won't be there because you're in early, but you're not a founder. Those 18 months, you A, know whether or not you enjoy the ambiguity and the unstructure, and B, you'll pick up tons of things that you wouldn't have normally picked up in a more structured environment.

this is sort of the, the test, and most people will actually say, well, I don't want to do that, why would I do that? But I'm saying, well, if you're not willing to do that, you're almost certainly in 12 to 18 months when you're even more successful than you are today, unlikely to take that leap of faith.

And so often, The question around when it's perpetually a year away, it's often an emotional challenge around having the courage. And I would argue that, you know, it's always harder to found later in career because the opportunity cost goes way up. You know, when I started, you know, my career and I found it and I was in four startups before I ended up going into a more traditional product management role.

There is very little for me to lose by being in an early stage. You know, the difference between going to a large company and taking three to five years to go through two or three rounds of promotion and going to a full, you know, in my case I joined an eight person company coming out of college and I had a choice between that and joining Sun Microsystems, which was a much larger organization.

And the difference is relatively small. You know, it was similar compensation. And I It happened to be a similar product area, and it was just a much wider role and a much more unstructured environment. But if I was a director or a VP, and the choice was between doing that and joining a startup, the distinction is massive.

And so the calculation, the risk that one would take, people say all the time, the risk is, I don't know if I'm ready for the startup risk. And what I define that to be is, are you ready to take the opportunity cost of giving up this relatively successful career in exchange to taking this leap of faith?

And so for me, I'm like, well, If I'm going to found, I'm probably going to do it once and if I'm successful, maybe I'll do it again and you want to make darn sure that that's a success. So you want to mitigate as much risk as possible. Your point is promotion doesn't build that skill. Your point is maybe joining someone else's company may at least give you that opportunity.

The earlier you go, the less you're risking in terms of compensation. The more you gain skills that can translate into future levels of career.

The observation I make when I look at people's career arc is they spend the first half of their career trying to fit into a system and maximize the system. And then the second half of their career, they get frustrated with the system and they wish they could kind of break out of it.

And what ends up happening is that means that they spend a lot of time trying to figure out what's the best company that I can work for? What's the best manager? What's the highest profile position? What's the biggest badges of honor that I can get as I'm going through these formative years? And then once they get into this management role, they spend a lot of time, perhaps even in the C level, fighting with the founder, trying to drive agency, et cetera.

What I would observe is You almost need to think about it upside down. At the beginning, your opportunity cost is low. what you realize is, look, you don't know as much, you're fairly naive. You have less to lose if you are the type of person that thrives in ambiguity and that doesn't need the system and that likes being hands on and that likes the idea of exploring, let's call it product market fit.

So wonderful time because worst case you go for a few years, you don't get anywhere and you decide that you're going to go back to more traditional. You haven't really lost anything. that much ground. And in fact, you've gained some skills that you wouldn't be able to have otherwise. And that's kind of what happened in my career.

You know, I joined a startup and we went through some acquisitions. A couple of years later, I was in a founding team. The founding team, I was sort of the lowest person on the totem pole. I was the youngest. I had done the least, but I really wanted to be in day one. And that company didn't actually go anywhere.

So five years in, I didn't have a lot of success, but it didn't really bother me because it wasn't like in. Four or five years I was expecting a ton of promotion and compensation or anything. But then I felt like I'd seen the movie enough that I didn't have a lot of fear to found. And then I founded and that company ended up getting acquired and I founded again and that company ended up at Google.

And at that time I realized I could get the bigger role. I could be more of a traditionalist and so that became more of the model. And so instead of trying to found in my later years and then being upset at myself because I needed the income or I needed the structure or Or I enjoy the management piece and not the product market fit piece as much

I felt like I scratched the itch earlier in my career and I felt like that model makes sense. And so maybe the thing that I would encourage listeners to do is. If they're early in their career, the default should be. Why are you not founding? I'm not suggesting everyone should found, but I think that they should go through this personal exploration that you're discussing.

What motivates you? What's your personal journey? Are you looking for an exit? Are you looking for an idol? Probably not. But find that personal journey, demand that answer of yourself, because if you happen to be good at it, you might enjoy it. Even if you made the same amount of money you might feel much better about your career in arrears because

you ended up going through this adventure, but then when you get to a mid to late stage of career, the default probably is not founding because the, the opportunity cost is high. The naivety is gone. The expectations that others have and the needs that you have are much, much greater. And so your ability to so called take risk is much, much higher.

And so it's almost the opposite of what conventional wisdom would say, which is in two years, I'll found. It almost like two years ago, I should have founded is the mental model.

Shreyas: Yeah. And I think the other aspect here to make this easier, um. And this kind of taking, because it is a big step. Heck, it's not even a step. It's like a leap to do it, no matter where you are in life. early or late, like it is a leap you need to just take. and you, you don't know for sure how it's going to work out.

You can increase probabilities and you should, but you don't really know how it's going to work out. but the point is that the skills you gain as a result, the experience you gain as a result, you have to have that faith. that it is going to to compound over a career, And that is sometimes hard to foresee.

The other observation I'll make is like, there is this tendency, certainly in the valley, there's this tendency to like, be fascinated with these big numbers, right? Like a hundred billion, 10 billion, 400 these are all like really big numbers. And most people, when they're thinking about this founding thing,

they just assume that it's gotta be like a venture scale. and so among the first things they do as they take this leap is of course, they're working on the product and maybe the founding team and other things, but they go out and like, okay, you know, pre seed seed funding.

and what I like to point out is that if you are doing this mainly for like an outlet for your entrepreneurial spirit, and if you're doing this because you want to create something of your own, you're doing this because you want to create a culture of your own, you want to create an entity, of your own that has only your fingerprints.

I want people to understand that there are many options available. Besides just going out and raising seed funding, and besides just the assumption that it's gotta be a venture scale, startup, Because I also find, through numerous, you know, coaching conversations and in some cases advising some earlier stage founders, the fact that they assume that it's gotta be a venture scale business.

Now they built something that is decent. They've built something that has. Some fit is, compelling in some ways, but now they're stuck because they've raised a bunch of money, and then, you know, hired a bunch of people, you know, uh, diluted their ownership, to a point where they feel stuck and, uh, you know, while this could have been an amazing.

You know, cash flow business. Now we've ended up in a place where you've created, uh, you know, more staffing, more just, you know, operational overhead, more burn. and frankly, like, A tremendous amount of stress, Because you made the assumption that this is the only path of an entrepreneur, right?

It is fine to start a more kind of traditional business, right? Where you are basically generating cash.

But the challenge people face is because the venture backed path seems more prestigious. and it feels really good to announce on LinkedIn, Oh, we raised our, you know, seed funding with these famous, famous angel investors and famous, famous, you know, whatever, uh, firms, and we see that all the time around us, especially in these tech centers, like the valley and other places.

And I want people to understand that there are more options available to you than that.

Nikhyl: Yeah. I think this is a really key point. And so maybe the we should start with like venture businesses exist because they have dollars to deploy. With the hope of very, very large outcomes. Most venture firms, the way that they return money to their limited is with a very small number of very successful outcomes.

And so their motivation when they put money into any startup is that this thing will return 10 to 100 X of what their initial capital is. Now, I think what you're saying is you decide to embark on the founding journey, you come up with a concept, historically, the concept that you come up with is highly connected and conflated with can this succeed as a venture business.

And it's largely because of the ego associated with venture, and also because that is what drives the lion's share of storytelling in technology. This company ended up having this big outcome, they took money from these folks, and then they ended up growing. And people often want to found, but their idea doesn't necessarily have the size and magnitude of a venture idea.

Nor are they even comfortable in operating as a founder in a venture backed system. Yet, I think the point you're making is in the past, that meant that they should not found or that they were stuck raising money and then running this system and chasing this huge outcome, which is frankly, very rare to succeed in.

Instead, what you're saying is, , Hey, I've got a concept. This concept is not a home run, but it also doesn't have the same risk profile as a home run, particularly with the advances in AI. Myself and two other people can build a pretty lucrative business.

Not only are you suggesting you should consider that as a healthy direction and potentially one to explore, but I would say, That financially, that might be a far more prudent outcome because a cash flow business, which may sound like, you know, getting on base a single, not swinging for the fences actually might one day lend itself to something bigger and more importantly, might be a lot more enjoyable and a lot more fitted to your skill and actually dramatically better for you than taking a rank and file File job at some organization.

And so what I've noticed is more and more of these opportunities exist, whether they're creators that are now exploding and having very successful careers and influencers all the way to the constant stories you see of a small team building something with using AI to help scale the organization. Not taking money and building quite a lucrative and quite a valuable business.

And those might be the most delightful businesses I love the idea of boy founding doesn't mean going to be a venture business.

Shreyas: The kind of business strategy view of this is If you can build a product solution service that serves a niche that pretty much every venture scale business is going to ignore because it's too tiny, but the niche does exist. And now if you can build something really compelling there, right, using all the same skills, the same product and business and commercial skills, that we've talked about, if you can build something compelling there, that can often be a very good outcome because essentially, what are you doing? You are avoiding competition altogether.

and whatever competition that may come up, that's also starting to now address this niche. Well, I have full faith that it's not going to be highly skilled competition, right? Uh, so you're going to beat them all day long, it's fine to operate in that niche, And like avoid competition altogether.

And, uh, you know, frankly, it's a great feeling of mastery.

Nikhyl: I think we've tried to debunk the myth around. It's often a myth to wait for promotion. It's often more of an emotional, uh, leap of faith than to an intellectual , I need a skill to be able to go forward. I think we've also spoken a bit about compensation and that we fully recognize that it's a lumpy, risky, different kind of compensation.

We've debunked the myth around venture as being the only way to found and actually be successful. The last one I wanted to explore is the, is the sort of conversation around burnout and the conversation around pace. the very widely believed truth that a lot of people will come to us and say, we're looking to found, but I think that I'm not sure I can deal with the pace of being a founder because, you know, I'm in this organization. I'm a product person. You know, I work in this so called cushy job. And now the idea of working 24 by seven as a founder is too much from a pace point of view. I can't put the hours in. Perhaps I have a family that I need to invest in and other obligations, et cetera.

How true is this concept between startups being dramatically higher in terms of pace than a traditional job in your experience?

Shreyas: I mean, it's the toughest job out there, right? To found your startup that doesn't get, tougher than that. if it weren't tough, why are there great returns and great satisfaction on the other side of it, why should you exit for a billion dollars or even a hundred million dollars or fifty million dollars? if it weren't tough. So, there's definitely that aspect and perhaps Nikhyl, I can share in response kind of like my own experience with, this category of question. it should be no surprise, for anybody to hear after this conversation that like, No matter where I've worked, I've always operated like a founder, and I've kind of usually created my own path, wherever I worked, even if I worked at Google, which is a very large company, obviously.

I created my own path, one of the things I realized as, because I have also, you know, gone through my own kind of journey of like, well, now's the time to kind of, you know, quit this and, you know, found my venture, venture scale startup. as I kind of just matured in life you know, reached a greater degree of self understanding, what I realized is hours work and work life balance, whatever we call it, work life harmony, whatever that is, is certainly relevant, but it's not the main way.

It's not the best way the question is really about how well you are able to compartmentalize, So now taking my own personal example, I am terrible at compartmentalizing, Meaning whatever I am doing right now, that dominates everything, right?

Like all my thoughts. So even if I'm not working, Right. Like if I'm not sending work related email or writing a document or whatever else that I'm doing, it's there, it's always there. you know, once I reached a certain degree of kind of career success, working within these companies, I also had to ask myself, what happens if I kind of found my own, again, like one of those venture scale startups.

And what I saw very clearly in my case was, you know, I was already working hard at, uh, you know, the companies I worked for, But there was at least a little bit of that separation, right, at times, versus I knew that if I found my own startup, it is literally going to dominate, even like, you know, sleep times, right?

Cause I, I had trouble sleeping even when I was like a product leader, so when I recognize that within myself, and then when I saw my life situation, and then, you know, saw that, my son, like, we have one child and, he's now 16, right?

So, this was several years ago, I still felt like, well, he's in the house for five or six years more, Do I want to spend these five or six years? trying to be more present with him, And again, it's not about the clock time, right? It's about what's here, or do I want to check the box of like, okay, I've started a venture scale business, And so now everybody can see that. Oh, yes, he has done that, right? And he exited it or whatever he did. And so in my case, the correct answer, like I said earlier, like usually in a specific case, there is usually the correct answer, We just have to like ask the right questions to figure out what the right answer is.

In my case, this question of balance and this question of like stress and burnout really came back to will I be able to be very effective at compartmentalizing? And for me, the answer was no. the same time, I know some people who are great at compartmentalizing, For them, the answer might be and will be different than it was for me.

Nikhyl: I like your note around mental focus versus clock time for a moment. So what I would say is one fallacy I've seen. Is that people that work in larger organizations, you know, whether it was stripe in your case or Google or, you know, I worked in a bunch of these larger settings.

We put in a lot of clock time, and I think that there's also travel time. There's also global teams, which means you're perhaps taking, you know, meetings off hours. There's annual reviews, quarterly reviews. There's a lot of expectations around being present and taking time. And so 1 fallacy that I've noticed is people say, Oh, well, founders, they work 24 by 7 while, you know, I could instead of doing that.

I can go work for. a big tech company and have this sort of cushy job. I'm like, most of the folks that I know, they're putting in a lot of clock time and there is a lot of energy spent. So it's unclear in your example where you have, you know, a child in, you know, high school, if even, you know, Being in one of those jobs would afford you the ability to compartmentalize and be present.

So I think one note is, I would not say that just because you're in a large structured environment or a mid stage structured environment, you're in a cushy role. I think that founder time is actually less structured time, meaning you're not in as many meetings. You may not be needing to travel as much.

You may not have, you know, 100 employees to spend time with, but it never leaves you because if you don't show up, The company progress is essentially, you know, static. It isn't moving forward. And so that burden, that responsibility, that emotional attachment, almost like a child, is very, very different. You can definitely not worry about the stock price if you were in a larger company every day that you decide to take a vacation.

Um, But if you are, you know, a founder, everything comes down to the energy that you put into the role. And that compartmentalization is quite different. But I think most people describe it as clock time, not, you know, occupied mental energy time or whatever framing you want to use. And I think that's a huge, huge distinction between the two.

because some people, like I was speaking with someone yesterday, they haven't been able to compartmentalize in their late stage role. They're, you know, very successful, but they work 24 by seven, not just in terms of hours, but because they're all consumed with this piece of software that they're working on.

And that person then would probably be the in the equal situation, but it shouldn't be a reason not to found because they don't know how To pull back and so you might as well take that as as an advantage. So as we wrap up thoughts on this or the thoughts that you want to sort of leave us with

Shreyas: can I share a really radical approach that I only figured out in the last, I want to say five, six years, before I started this new chapter of my career,

this is not for everyone, but, uh, I loved doing it. Okay, so here it is. So you're right, Nikhyl, if you are operating at very high levels in tier one companies, uh, and they could be very large companies, I know Google, meta, Amazon, et cetera, and certainly like fast growing companies, whatever those might be these days, you know, highly promising fast-growing companies, There is a way out. And you can get both. Okay. But you have to follow and you have to be okay with this radical approach.

So what is this radical approach?

These jobs are very busy. You are right. And they are all consuming. But if you want to still be able to find that balance, sometimes temporarily, right? Like, say, this example of I'm going to be an empty nester in five, six years, And I don't want, this thing to become all consuming work at one or two levels below what you normally would

what happens is the reason these things get all consuming for us one because of scope scope just is like a massive force that is going to obliterate anything but the second is the competence and the mastery we're used to all of us ambitious people.

We're used to working in a role and at a level which is challenging us just right, right? And challenging, challenging us to a high degree. So what I decided to do in the last five, six years before I kind of exited the corporate world altogether, is I consciously decided. Yes, I want to work in fast paced companies.

I want to work in like, you know, I want to work on the most important businesses or build the most important businesses from scratch at these companies, et cetera, et cetera. But I'm going to work about a one level, at least one level below what I actually can. now. This is radical because it goes against most, career advice out there, but I'm so glad I did it.

Nikhyl: Oh, this is so brilliant, man this is such a courageous move because you're note and so this would be an incredibly effective way to retort the You know, I feel like I keep getting more responsibility Responsibility Because I succeed and then I burn out and your point is whose fault is that the company is rewarding you because they think you want more work.

The only person that could essentially set the quote unquote boundaries yourself. What is the downside of having smaller responsibility with greater skill and perhaps more time to bring back to yourself? The downside might be perceived compensation, but oftentimes the compensation that you're receiving is highly connected with the growth of the equity in the company.

And so in some ways, the fact that you end up with, you know, 10 percent less in earnings, but the company's stock is really the one that fluctuates 50 percent every year is going to have a much greater factor. But then you might have a three year additional tenure and you might be able to see your kid and yet it's considered to be almost an irresponsible form of career advice because you're not taking the biggest job at the best company in the hottest role.

that's powerful. I think the other thing that you've said to me that I thought was really powerful is if you reverse engineer, what drives a lot of these challenges around burnout. You realize that a lot of the time we're spending moving paper or, you know, organizing, you know, information for someone else.

I mean, you spoke about this at the Lenny and Friends Summit as well, our creativity is not being deployed in a sufficient way. And a lot of the people that are here, and particularly in product, You know, they're creative humans there. They're in product because they want to build. They want to be creative.

One of the things that we don't discuss about founders is in a world filled with ambiguity. You get time to spend a lot of energy doing creative work. Now, some of that is creative work that doesn't play out that you fail. You end up building things you throw away, etcetera. But you may not feel that it's work in the same way that putting together the quarterly review doc or going through planning feels like work, you know, trying to solve some interesting product problem and then throwing it away or talking to a customer that is like really interested in the thing that you've built can be very key.

You know, energizing. And so these are the like the nuances around this sort of founder burnout that I think people don't discuss as much. Instead, they just sort of go to this sort of, Oh, you know, I want to be a Steve Jobs is one reason to found this is the. Founding just means more pace. I can't do with that at my point in life.

Meanwhile, they're burning out in their cushy job, and they're taking on more responsibility for less pay, you know, ultimately is what's happening. So I'm really hopeful that the audience has a chance to sort of embrace what Shreyas is saying around how personal, the journey is and how you have to ask these core questions and you have to sort of understand what is these risks that I have to take?

What are the journey, the steps that need to exist in the truths that need to be held in order to go through this? So, I couldn't be more grateful for your time. This was a fun and terrific conversation. I think many, hopefully many. Good founding decisions come out of this, whether it's people starting companies or staying and feeling more secure and staying in their organizations. So if people want to connect with you, find you, follow you, or spend more time with you, what's the best way to do that?

Shreyas: So the best way is to just follow me on LinkedIn or Twitter YouTube. And the things I share on YouTube are somewhat different from what I share on LinkedIn and Twitter and even threads. so definitely that's a good place to start. And if you've already been following me and you want sort of even sort of like more advanced views on things, things I do not share or have not shared publicly, you know, I, I teach a couple of courses.

Uh, they're very different than, you know, most courses out there. So you can check those out as well.

Nikhyl: I think a lot of people that are thinking about founding think a bit about, uh, I would found if I had an idea. And I think that in some ways it's less about the idea and it's more about the journey to find product market fit in a specific market.

I wonder, you know, how many founders or maybe founder wannabes. Are finding value in your product sense course, because one action that many of our listeners could take is they could say, I can see myself, you know, going through this founding journey, but I'm not sure if I have the sort of producty skill enough to go through it.

Do you recommend the product sense course or the career course or how would you map to some of your content to help them through that?

Shreyas: Yeah, so the Product Sense course has been taken by, at this point, over a hundred founders. and so those would be, uh, CTO founders or CEO founder. some really world class founders have, uh, taken it and, found it, uh, to be extremely unique, uh, and very valuable for their own companies. A few of them have since, basically made it, uh, available to their entire company, their entire startup, just because they found it, uh, very valuable.

and one of the things that, uh, my, you know, the founders who take the course, especially like these are like very talented product founders,

One of the things they have observed fairly consistently is that, um, they give me feedback and the feedback they give me is, Shreyas, you are severely underselling, the value, the content and the benefits of this product sense course, because it's about so much more than that, to which I say, yes, it is very intentional.

because, I really want people who are authentically interested in learning about the correct ways to make product decisions. And I don't teach processes. I don't teach, Oh, here's a playbook of this famous company. And here's a, cause none of that works. Process doesn't work. Playbooks don't work. They are entertaining and they're placebos.

They are, uh, very tasty placebos, but I don't teach any of that. I teach skill. I teach the skill of making correct decisions about your product, the skill of understanding what the customer truly needs, the skill of figuring out what your true strategy should be, not the rara fake strategy that we write like these people.

You know, beautiful flowing documents. They're not saying anything, right? Like, what is real product strategy? What is real segmentation? What is real differentiation? and then I also teach product creativity, which is like most people think it cannot be taught, but I actually teach it in the course. So after going through that experience, it's an intense experience, but after going through that, a number of founders tell me that like, Whoa, like I, I had high expectations, but this ended up beating those high expectations.

the course is intentionally under promising. It's called improving your product sense. That's it's that's what it's called. It's not even like, you know, I had many options. I could have called it mastering product sense and. You know, getting to product market fit and whatever else, but it's intentionally called improving your product sense because I want to attract the right kind of person who's genuinely interested and like is sort of like self aware enough, and humble enough that, uh, they want, to really learn this skill.

and it's been really fun, uh, to teach it already. I just started, uh, earlier this year and, uh, I teach it every month. Uh, and the other course I teach is, more for like product people, PMs usually, uh, for kind of basically making correct decisions about their career. So that's where I go very deep on a lot of things that I've found, even very talented product people, make.

poor and incorrect decisions for their own career. and so this one's a shorter course. It's just over one weekend where I walk them through correct ways of thinking about your career, correct ways of making career choices for yourself, and then progressing, on that path.

Nikhyl: I mean, I think both of those are super career additive for our listeners, for my listeners in particular, but what I would say is if you could theoretically, given how important getting product strategy right.

This course could be a terrific way to enable that. I mean, if a hundred active founders are taking it, you can imagine how many wannabe founders should also find it a value. So hopefully that's something that many of you check out and, uh, Shreyas, thanks again. I really, really appreciate your time today.

Shreyas: This was really fun, Nikhyl. Thanks for having me.