Edu: Founder Failure - 7 Archetypes Destined To Destroy Their Own Companies

Chris: No founder obviously is born an incredible founder. Every new business that you start requires different things from you and the company. And so some of your muscle memory may not apply as you say, you can't read the label from inside the bottle.

I like that metaphor even if you're an incredible founder, you're an incredible multi-time founder, you know this domain very well, you still may be too much in the weeds, too close to the problem to really see the full picture.

Chris: Hey, I'm Chris

Yaniv: And I'm Yaniv

Chris: And on today's episode we wanna discuss the seven Archetypically terrible founder traits that can infect and destroy startups. Listen carefully and with an open mind because you may be unknowingly ruining everything for your company.

Yaniv: Now just before we jump in, I can't wait to do this one, but I'd like to remind you of the Startup Podcast Pact and to make a specific request. This week we've started a mailing list and we're going to send out a weekly wrap up of all things T S P. We're gonna have episode sneak peeks, other content from me and Chris Invitations to participate in T S P initiatives and more. In fact, we're gonna have some special content that's only accessible to people who joined the mailing list.

So go on, hit pause, go to TSP show and sign up now. We'll wait, won't we, Chris?

Chris: No, not waiting.

Yaniv: No, not waiting.

 Chris. Let's jump in.

Chris: All right. Awesome. today, as we said we wanted to talk about archetypal traits of founders that can ruin their whole company. Now of course, these, traits are not just for founders. Any person in leadership can exhibit these traits and really undermine their team.

They're part of the company, but they're particularly pernicious when they come from founders, because founders have a kind of cultural clout, which can infect the entire company. It can be the original sin that breaks everything, that really stops the company from hitting that hockey stick growth raising capital and surviving very, very long at all.

And so it's particularly important that founders pay attention to these ones. But if you're in a position of leadership, in any size company, anywhere, you wanna watch out for these, blind spots and these very, very bad behaviours, as we go through them.

Yaniv: Absolutely. But I'd actually like to go a little bit further, Chris, because I'm in a position where I have worked for many founders. I have interacted with people who've worked for founders as an investor, as an advisor, as a mentor, and then I've become a founder myself. what I've seen over the years is that everything that is amazing and wonderful about a startup comes from the founders in some sense.

But the flip side is also true. Every problem, every weakness, every dysfunction of a startup can be traced back to its founders. and there are lots of ways to go wrong. And so, In a sense, the genesis of this episode was as a founder who has worked for founders, I'm quite paranoid. I'm like, which one of these am I going to be in?

What ways am I, my co-founders potentially going to sabotage our own company because we don't have the self-knowledge to see the different ways in which we can go wrong? I think it's very rare that founders have bad intentions. It's very rare that they're not doing their best.

The issue is a lack of self-knowledge and bad habits. Often strengths that become weaknesses that then hamstring the rest of the company. Its ability to grow as an organization and that is something that's very scary. And so what we want you, as founders who are listening to think about as you listen to this, is, which one of these am I at risk of becoming?

And what can I do to make sure that I don't, so that we can have an incredible startup, an incredible company that is fun to work at and changes the world and gets us the outcome that we want.

Chris: you're right, y Evan, I think as we touched on it's bad for any kind of leader, but particularly pernicious for founders because it may not be the behaviour the founder is exhibiting that breaks things directly. It's not like they go touch something and it breaks Although that might happen too. It's sometimes that it's a subtle dysfunction that permeates the culture. And then when everybody starts to do it, that's when the, whole culture is suboptimal and, breaks at scale. And so it's, not just, Hey, I'm going doing something. And that thing is, resulting in an immediate feedback loop.

It's that, tendency to hesitate or that tendency to, overindex on sales or that tendency to, overanalyze and we'll go through these that permeates everything and then at scale starts to be a real, drag on the company as well.

Yaniv: Absolutely. And, and the final thing I wanted to say before we jump in, I promise we're about to get there, is that one thing that some founders struggle with when they, think about this is there's a kind of a, humility, not a false modesty, but an inaccurate modesty where you're like, oh, what little old me?

I'm just me. Like, how can I have such a big influence on this whole organization? I've seen this when I give feedback to founders where I say, you have to be more careful how you comport yourself in this meeting or what you say, because it is massively influencing how everyone on your team around you is acting.

And they're like, oh, but it's just me. I'm just, giving my 2 cents. And it's like, yeah, but you're the founder and whether you like it or not, some people like it. A lot of founders don't. Whether you like it or not, your voice is very loud. People are listening carefully and people are taking cues from you.

And so accept as a founder that within your organization, when it's small at the beginning, but also when it's big later on, you are very influential. And that is not arrogance, that is realism. And that is a heavy responsibility that you need to wear carefully if you wanna have a successful startup.

Chris: Yaniv, you obviously mentioned voice specifically there, and this is perhaps obvious, but it's not always spoken explicitly, right? It could be body language, it could be in the decisions you make or choose not to make. it could be in the people you promote or pay attention to, or spend a lot of time with, right?

And so your values, your behaviour, your priorities, these things become clear, even maybe if you're not saying them explicitly in front of other people.

Yaniv: That's right. It's a bit like parenting really, isn't it, Chris? We're both parents of young children, and whether you like it or not, you have a lot of influence over your kids. They are watching you, they're learning from you, they're modeling themselves on you. And being a founder is a lot like being the parent of your company.

It's an analogy that we've used before. We'll come back to here let's jump in,

We have seven founder archetypes that we're gonna discuss, and the first of those, Chris, is the showman. So tell me what the showman or show person, is actually like.

Chris: Yeah, well, the show person, is a person who is a really, really great storyteller. They love spinning narratives, they love framing and positioning, and, putting together and connecting dots between this trend and that trend, this idea and that idea, this problem and this problem going all the way back to the root and spinning wonderful tales about how all these things are related to this other thing and how they're gonna go about solving that problem.

Problem here, because storytelling is really very valuable, in a company, is that. Either they don't get past that point and they're just going around telling stories, or they're so enamored with the storytelling that they keep coming up with new stories, different stories, better stories. in both cases, the storytelling becomes the thing and they think the storytelling is the value creation.

And as soon as their story makes contact with reality, reality being hard work to create value or reality being telling someone the story and then hearing some feedback or some addition, they instantly kind of start reformulating the story instead of pushing through to move forward towards the next stage, which is execution.

Yaniv: I was actually talking to someone just earlier this week about this and I mentioned Chris. Often a lot of these archetypes come from strengths that are too strong and become a weakness. storytelling, like you said, is really important. We have a whole episode about storytelling. We have another episode with Navaro about his book, fuck the Slides about Raising Capital, and it is so important to be able to tell stories to your team, to be able to tell story to investors, to be able to tell stories to the media if that's part of your growth strategy.

But if you're too good at it, you can start to get a bit high on your own supply. It gets too easy to raise money just by telling great stories, by spinning this amazing web and you raise money and you don't spend that money very well. But that's okay because the next time it comes to raise, you can tell another amazing story.

It's a different story, but people buy it again. Now you can get a lot of rope here, but eventually, You're gonna get to the end of that rope and it's gonna snap back. It's gonna be really painful because you haven't built an amazing product and amazing business that actually is the culmination of that storytelling.

And so I often say that as a founder, what you kind of wanna be is quite good at raising capital, but not too good. Because if you're too good, you can end up thinking that raisin capital is the game. Raisin. Capital is not the game. It is a means to an end. And the storyteller gets so enamored, so caught up in, I tell beautiful stories.

I get capital, I get featured in newspapers. My team is inspired by what I say. And you can keep that going for a while. It doesn't last forever. Now, I'm not saying turn down your storytelling. If you're a good storyteller, do it. Be a great storyteller. Use that skill, but never get high on your own supply.

Never believe your own bullshit too much because that's when you get disconnected from reality and you forget that the hard work is to build and build something amazing, and the story is just something that gets you the opportunity.

Chris: In that example there, you are really talking about the very best storytellers who know how to tell stories about pain and problems and commercial realities. And they might be actually successful at raising capital. there's even a worst kind of storyteller that I'm thinking of whose stories attract communities.

They attract people who are a little bit woo woo, right? They're a little bit, fanciful and magical thinking and they're not really very commercially savvy. and they get a lot of positive feedback from their community and from their friends and their enthusiastic supporters. But investors, see right through it They're like, this guy is telling, a wild and interesting story, but. Where's the rub? Where's the commercial reality? Where's the problem? those founders who are maybe not so commercially savvy, they're just pure storytellers, they will be struggling to understand like, my vision is so big and so grand and so epic and so clear.

Why can't I raise money? my community's telling me it's amazing. And, they're so positive and, still I'm not getting any commercial success. And they can, start to get very bitter. These people who tend to be very, very wonderful people, amazing hearts, fund to be around, can, can actually get quite bitter their story is so captivating to their immediate friends and community, but so commercially unsuccessful.

Yaniv: You are right Chris, that it's a bit of a different scenario, but actually, in my view, it's very much the same thing. You know I talked about you can have a lot of rope. I think the better the storyteller you are, the more rope you get. But the rope is always. Finite in length, and eventually you reach the end of it and then you get pulled back painfully.

So an okay storyteller might never get to the point of fundraising. an amazing storyteller can get to the point of raising multiple rounds or even the verge of I p O. In fact, we had an episode on Adam Newman, the founder of WeWork, and it's quite topical for this because at the time of recording it's, August, 2023 and WeWork just issued a solvency warning.

So this company that was once valued at, $54 billion was trying to, I p o at that valuation is now worth less than $300 million and may not be in business by the end of the year. But Adam Newman told such a captivating story. He could get all the way there, but even for him, he reached the end of his rope, got pulled back because WeWork was not the business that matched the story he was telling.

So really it's a bit of a blessing if you're not as good at storytelling, because if you're that good at it, And you believe your own stories, you can go for a very long time, without realizing that you haven't built anything of value. Now, Adam Neuman's a billionaire, so I don't feel too sorry for him.

But, nonetheless, the point stands,

Chris: All right, let's, uh, talk about the next one. the next, founder archetype that is ruining everything is the sex addict. now this is really not the sex addict. This is the sales addict, someone who's never seen a deal they didn't want to close, and is really too obsessed with sales to actually scale their company.

we've had of course episodes about why scale is important, so we probably won't re-litigate that here But, Yaniv, tell us about the sales or sex addict.

Yaniv: I mean, the term sex addict actually comes from a, founder. I, did used to work with name will not be revealed to protect the. Innocent. but yes, this idea of, pursuing deals and yes, it's, sales or sales adjacent, it can definitely manifest in sales. Where it manifests the most, as I see it, is in partnerships and business development, which is, which is a type of sales, right?

partnerships look amazing, Because you are talking to another business and it's like, I scratch my back. You scratch your back. We'll give each other, each other's customers.

It's gonna be amazing. That usually doesn't work. It sometimes does work. It can sometimes be very powerful, but there are two ways it doesn't work. One is you really want it and the other side doesn't want it as bad, but they're too polite to just reject you cleanly. So they string you along, but they never fully commit.

The other is the collective delusion, and that's what you don't realize is partnerships are normally between two businesses to sell to a third party, which is a set of customers, right? And both businesses can genuinely believe that they have a synergy because they both have dollar signs in their eyes.

They're like, this is great. We're gonna make lots more money. But no one's actually asked the customers if this partnership is valuable to them. And so they finally go to market and nobody wants the thing, right? The problem is you have this massive optimism bias. but also the problem with deals, whether it's business development or sales, is they have dollar numbers attached.

And because they have nice upfront dollar numbers attached, it's like, you do this deal and you'll get a million dollars. You never look at the cost, Everything has a cost and a benefit or a return. with these deals, it's often like you see the return, but then you're like, oh, the engineering team will just build this.

And you sort of stuff the actual expense into a place where it's not as transparent and you can pretend it's not there. But of course that expense is there. So you stuff too many deals down into your team and they can't deliver and nothing else happens. And then you become that old story, Chris, that we won't belabor you become a technology backed services business, because you've just done all of these deals and you haven't actually got your own product roadmap.

You have relinquished control over the product that you're building.

Chris: Yeah. , some of the psychology in some of the cases is they perceive the actual.

Hard work of sales to be a little too hard, and they don't want to be involved in that, dirty work of , sales, bringing customers along. And so they want to kind of skip the line and work with someone else who already has the customers. and I'm often fond of saying, sell your own shit.

Like, figure out how to get your stuff into an end user's hands, and stop trying to rely on distribution partnerships I hear people talking about franchises, which is a whole other episode we should talk about. the feedback loops are too long. The incentives are misaligned and, it's not as easy as you think it is.

In fact it's incredibly, incredibly difficult. So, sell your own shit and stop trying to make deals with middle people. and also be careful what you're selling because, you may be selling the wrong thing in the wrong way and, it will never scale.

Yaniv: There's one final thing to mention about the sex addict archetype, which is they can be really demoralizing to their team because remember, you've got a team, you've sold 'em a vision. You may be a bit of a showman as well. Remember you can, represent more than one, archetype.

But general, people have joined you because you have a mission to build something somewhat transformative, right? You're a startup and then they're sitting there and you just come to them saying, I promised this partner this, and I promised this customer that, and you have to deliver it by this date, and.

You take away the team's agency nearly entirely and worse than that, you are creating hard deadlines. So startups generally have soft deadlines. They can be agile, right? They're like, okay, we need to move fast and iterate fast, but we haven't made commitments to anyone. As soon as you have a sales cycle, as soon as you have bd, you're making all of these commitments that they're often unrealistic because the team is often not brought into these discussions, and then you just jam the shit down their throats you know what?

They're not gonna be happy. So you end up often with morale issues and attrition issues if this is how you operate your startup.

Chris: This is beautiful, segue to our next archetype, which is, essentially the worst version of this yev, which is we're calling them baby Elon, who is so uninvolved in some of the essential details that they don't know the costs, they don't know the complexity for actually following through on all the commitments or ideas or strategies that they've come up with.

Now, I wanna be quick to point out here, you know, We're talking about Elon Musk here, of course.

Yaniv: Any other real lines out there? Raise your hands.

Chris: you know, can be very, very involved in the details actually in terms of, making choices about rockets and, deleting features from Twitter.

But he also makes a lot of promises in the public, on stage, and can flip from idea to idea, the Roadster to the cyber truck, to the, badge on Twitter and the whole team's scrambling to make it happen. And, Elon is a little bit of a magical unicorn.

He has enough money and enough clout and enough people but many founders are, Crazy ambitious and are crazy running from idea to idea, and not engaged with the true cost and the complexity and the time it takes to build something even mildly useful by the r and d team, the marketing team, the biz dev team, and the sales team, and so on.

Yaniv: Yeah, I mean, to be clear to your point, Chris, I think we're really talking more about Twitter. Elon like Tesla-Elon and SpaceX-elon apparently needs a lot of managing up, but his involvement in the details, at least at times, has been really valuable. Twitter-Elon has basically made a bunch of unrealistic promises, had a bunch of absolutely failed product and feature launches because he has been unwilling to listen to his own team and understand the complexity of what he's asking from them.

He's got a very, Simplistic idea of what it takes to build features into a social network like Twitter and I guess the warning sign of a founder like this is, they'll say, couldn't you just, or it can't be that hard, these are your little telltale signs of a baby. Elon. I think every founder is guilty of this a little bit, but I think what is interesting or differentiates them is what happens next when you as a founder say, couldn't we just do X?

Or it can't be that hard, and your team pushes back, do you listen to them or do you just run roughshod over them and say, Nope, we're just doing it. We're gonna launch it next week. Just get it done. Right? And then what happens? Well, you get an underwhelming launch, you get technical debt, you get things that break because you have just not taken the effort to understand the details.

But I think the other bit of baby Elon is, they're uninvolved in the detail, but they're very directive, they're very top down. Right? You have other types of founders who are like, well, you know what, I'm not across the details and I'm not really interested in the details. I'm not interested in the product that I'm building.

Right. And it's not one of our archetypes, but you do get founders who are simply uninvolved. I think the, thing that marks out a baby Elon is that they are involved, but suffer from a type of magical thinking that if they're just gonna be hardcore enough and like, push their team enough that all of these challenges and difficulties and costs just go away through sheer force of will, and they just don't.

Unfortunately, it would be great if they could, but they don't.

Chris: and I think you're talking about the best case scenario here, Yaniv, where you get a lot of technical debt and something's break in production. I think if you are sufficiently, bullish Sufficiently a bull in a China shop, oftentimes nothing ships because people are just running around like chickens with their head cut off and don't know what to do and how to do it.

And they're underestimating requirements and implications and they're just like, Half building stuff and Oh, no, wait, that's not right. And then they kind of build other stuff and it is like, and everyone just has no idea what to do. or you have 5, 7 17 initiatives or strategies. And, the resource contention is so high that nothing actually gets done.

Because every department, every strategy, every initiative, every business is pulling in a different direction. and so very often the answer here is to cut, cut, cut, all of the nonsense and focus on a few things and doing those well. Or if you're in a lucky position where you're a great storyteller and you've raised a bunch of capital, then you need to rightsize the team.

And oftentimes that's a, team that is far more expensive than you imagined. it is , you know, fully staffed squads with product managers and engine managers and engineers and data scientists and product marketers. 'cause each of these things is its own product initiative and you need to staff it properly.

And so I'm often fond of telling the scale ups I work with. Like, either you need to slash 80% of this, so you need to grow your team by 80%, but one or the other, or it's not gonna work. and it's a very painful reality.

Yaniv: So I think one thing, maybe at this point, Chris, is to say, well, If you are a founder and you're worried that this might be you, what do you do about it? And I think it comes down to, well, okay, we talked about being too uninvolved in the details. And founders often get this, feeling.

It's a vibe. It's like everything's going too slowly and maybe I don't quite believe that my team isn't able to execute faster. And they're like, I'm just gonna push them. We're all gonna be extremely hardcore and just move faster. And then, They don't understand the costs of doing that. So I think a lot of it is getting across the right details.

And we are gonna come in a couple of, archetypes to the helicopter parent. it's about getting into the details in the right way, right? Which is not micromanaging the details, but knowing the difference between something that is hard and something that is easy. And a lot of that is also about building trust with your team, depending on what stage you're at.

You know, if you have, VPs or execs or C-level and they're running their teams, listen to them And manage them well because that is your nexus for control. But if you've just got this feeling that no one's ever working hard enough and everything's taking too long, but you don't actually get enough into the details to understand, to be able to call bullshit.

So you just assume everything is bullshit. That is when you become baby Elon and it, does not help anything to happen.

Chris: So I actually wanna disagree with you a little bit here, Yaniv. I think if you're in a scale up and, you are, trying to figure out why your team has slowed to AC crawl and nothing's getting done. And, I find founders and boards and leadership teams are always like, we need more detail.

Where are the dates and where's the roadmap? And we wanna see exactly what's happening and give us the details. And they ask for more detail. And they don't actually have the means to interpret or understand or, digest or act on any of this detail. What they actually need is to talk to someone who knows what the hell they're doing in terms of organizing a team and right-sizing a team and designing a team for success and, fitting it for the number initiatives and businesses they've got.

And, you know, you talk about understanding what's easy and what's hard, again, particularly at the scale up stage where you have obligations and you have, customers and you have regulatory requirements. let me save you the effort to figure out what's easy and hard. Everything's hard.

Everything you want to do, right? Like, no. No, seriously. Like everything you want to do

Yaniv: No, you're completely right. Yeah. You nailed it.

Chris: Yeah. Everything is gonna,

Yaniv: touche.

Chris: Everything is going to take a quarter, right? Every new feature, every new initiative is gonna take a quarter and every business, every, theme, every goal is gonna require 1, 2, 3, 4, 5 teams.

And if you think I'm crazy, you are crazy. Right? you need to

Yaniv: You're not crazy. You're You're,

Chris: Yeah, that's right. Naive. and so this idea that like, well, we need more of the details. Why is things going wrong? Well, because you have seven initiatives or six business units and you have five engineers.

That's why. that's the problem. So no amount of detail is gonna fix that. find a chief product officer who can tell you to go to hell, we have a whole episode about saying no. and you have a lot of teams who are like, yes sir, I'm on that. Yes sir. I'll get that done. Yes sir.

We'll find a way to do that. And they're a bad leader. They're not giving you the signal, which is, you don't need more detail from me. What you need is to hire more people from me or to shut down these dumb nonsense initiatives. And you can hear me getting fired up about this because oftentimes ya I will see teams saying, we just need more details.

Where's the details? Where's the roadmap? Where's the tickets? Where's the estimates? And, they don't want the detail. They just wanna find a way to fit, a hundred pounds of work into a 20 pound bag.

Yaniv: And I think that's like that analogy of like trying to stuff more into a container or a vessel than it can bear, I think is, very accurate. you just, can't get it all in there. When I was talking about the detail, it's also about how you use the detail, and maybe I'm talking about a more advanced level here, right?

Which is, I think there's actually value and I'm finding value myself. I'm spending a bit of time getting a bit deeper into our architecture, not so I can like. Yo-yo in and, make everything messy, but so that I can have a better intuition about how hard various things are so I can stop being a pain in the ass.

Right? So I, can just have more context upfront. but you're right, that's probably at a, higher level of abstraction than the basics, which is, yeah, more detail is not gonna help you as a c e o, as a founder, to get your team to move faster.

Chris: That's right. is not gonna help you fit, too much stuff into a small bag No amount of detail is gonna solve that fundamental impedance mismatch between those two things.

Yaniv: So the next archetype we have is called the Grownup. This is one of my, personal favorites because I've always felt, somewhat. Talked down to by grownups. Grownups are the type of person who, they may have done an M B A, they may have worked at a large corporation. they know quite a lot about finance and p and ls and, and stuff like that.

They don't really understand venture backed startups though. So they get a bit obsessed with forecasting and, revenue and, that sort of thing. And they're like, let's run this startup like a real business. This is how it's done in a real business. And, you know, going all the way back to episode one of this podcast where we talked about small business syndrome, the grownup might not think they've got small business syndrome.

Might think that they've got big business syndrome, but really this way of thinking at an early stage is dooming your startup to not being venture backable, to not being that high growth story. Because what the grownup believes they have is control and predictability and startups. Are characterized by a lack of control and a lack of predictability.

That's why all of these methodologies around lean, around agile, around being iterative, around talking to your customers, they're about making progress in an uncertain environment. The grownup by denying the existence of the uncertain environment, creates an environment of false certainty and false precision, and they feel good about that.

And when other people say, Hey, we can't know this stuff, it's unknowable. they say, you are deficient in your grownupness. And if you just tried harder, we would know what our revenue would be in 18 months from now. And this can be really harmful because it means that you have plans and roadmaps and forecasts, and you spend lots of time talking about why you didn't hit your forecast.

Instead of talking about how you actually make a great product and a great business that can grow, at a higher scale.

Chris: Yeah, I, spend a lot of my advisory work, Managing grownups, managing this, archetype. And, maybe it's my own psychology. I'm, sharing too much information here, but I've never felt much like a grownup. I always pride myself on being young at heart. but yeah, even though, you know, I've been doing this now for two and a half decades, and I'm very much, often the, older person in the room, particularly if we're talking about below board level.

And, yet there are people who are ostensibly, younger than me in age or on a board in a position of authority teaching me how, the grownups do it. that's interesting in theory, Chris. So that might work for Silicon Valley, Chris, or, uh, we need to understand where this business is going.

And can't give this away for free we need a value exchange.

Yaniv: Another way of maybe characterizing the grownup is there's this great meme template on the internet. I'm sure a lot of you have come across it, the mid whit meme, right? And so it shows a bell curve of intelligence and at, one end of the bell curve at the left side, you've got the dumb person, not very intelligent person, and they say, oh, well, just listen to your users.

And then you go up to the middle of the bell curve and you've got the mid midwife who's like, do cohort based analysis and, 18 month forecasts and focus groups and blah, blah, blah. And then you go down to the extreme right of the bell curve of the super intelligent person, and they say, just listen to your users.

Right? And point there is the person of middling intelligence and high education can get overly analytical and overly caught up in the superficial complexity so that they cannot understand the fundamental simple truth that both the simpleton and the genius can see.

And so I think the grownup is often the midwife in this scenario, right, where they, focus on this superficial complexity of running a business rather than the beautiful simplicity of trying to create a real wonderful solution for a real problem that exists in the world.

Chris: Yeah, interesting 'cause this, reminds me of a different kind of grownup, a grownup that has grown up around startups and grown up around the, traditional or academic school of product management, which is, everything is is a hypothesis and a test and an experiment.

And, the grownup things to do is just listen to your users, as you said, yev. that's both the simpleton and sophisticated answer. But find these kinds of grownups who've studied product management and design-led thinking, failing to do the most common and most basic thing, which is to.

Look up from the map and actually observe the terrain need to test how to do shopping carts. well actually there are like two decades of, examples in the wild of how to do a shopping cart. So no, you don't actually need to test that. There's this sense of unreality where everything is a new idea everything needs to be tested. You do not need to run an experiment about something that is plain as the nose on your face build it, ship it, and move on. and so this is a new kind of, uh, grown up, the startup grown up instead of the N B A grownup.

Yaniv: There are many types of grownup, and by the way, being a grownup is awesome, right? But you wanna make sure that you've learned the right lessons and you understand how to apply them in context. Now, the next archetype is what I call the helicopter parent. And this is actually something that happens when a startup gets much bigger, gets into, you know, the large scale up territory.

And for me, the, sort of formative story, and I may have told it before on this podcast, we don't remember everything we've said anymore. good news. It's probably neither do you listeners. but. When I was early on at Google, I was engineer number 3000 or something.

So, you know, it was not the early days anymore. This was 2006. obviously it was a much smaller company than it is now, but it was still a very large organization. Now, Larry and Sergey are incredibly smart people. Those are the founders of Google. and they were used to always being the smartest guys in the room with the most context, the best insights and, you know, just amazing, right?

So they would come into a room with a team and say, Hey, just show us on a whiteboard what you're up to. And then Larry and Sergey would come in and just magically drop a couple of amazing insights and the team would be like, that's amazing. And they'd go away and like, build a thing. And that's how they ran the company.

Now, like I said, we had 3000 engineers organized into, I guess what, 600 teams by the time I joined Google. But Larry and Sergey were still doing these reviews, but of course with 600 teams, they were maybe having a 15 minute review once every six months or so, and they had no idea what we were doing at the start of the 15 minutes.

And they had very little idea what we were doing. By the end of the 15 minutes in particular, they didn't understand all the complexity, all the dependencies and everything else that an organization that Google was at that size by then would have. And so they would give us bad advice. These truth bombs would no longer be truth bombs.

They would be just like the sort of advice you would get from someone who'd spent 15 minutes learning about your project. In other words, not very good advice and. Then they would leave and never follow up. when this happened, I said to my manager, I was a first year, you know, graduate employee engineer.

I was like, what do we do with that? terrible advice that we've just been given. And he is like, oh, just ignore it. And I'm like, I can't ignore the founder of the company, the billionaire, unicorn pony wizard, Sergey. And he is like, well, but you know, it's just not realistic and he won't remember anyway.

And I thought, that is so sad that, this person who is clearly a brilliant founder, a brilliant computer scientist, a brilliant engineer, had become irrelevant by failing to scale with the organization. I call it a helicopter parent. It's like, a parent of a 15 year old who's still treating their 15 year old like they're three and trying to wipe their bottom and so on.

And you know it's not gonna be welcome. It's not going to help that 15 year old be the best version of themselves. The parent has now become a liability and an embarrassment. And it can come just from these good intentions from the fact that this is your baby, but your baby's grown up and you have to relate to it differently.

And if you don't make that pivot ' cause you're like, Hey, I was the C E O, then I'm the CEO now, ? But no, your job is totally different. The way you need to approach your job is totally different. And if you don't adapt your style you don't let go and you become an irrelevance and an inconvenience.

And in the worst case, a bit of a joke internally and a person just be avoided and kind of coddled. And basically people practice harm minimization around you. is that really what you want for your legacy?

Chris: The trick as you scale up is to fall in love with building the thing that builds the thing. and building an elegant. Company with an elegant, org structure with an elegant, process for planning and execution can be just as delightful and interesting, a challenge as building a product, in some cases more so.

And so making that switch as a founder from startup to scale up, it can be difficult to know when to do it, how to do it, how you need to e evolve and change yourself. And of course, it's not about like letting go of the details. You know, we've talked extensively in this episode about being engaged in the right kind of details.

It's about having the right. Org structure and ways of working such that you can set the agenda and you can set the principles, and you can set the key goals, and the context and, the terms of alignment across the company. And you can have key lieutenants who can give you the right abstraction of information and who you can share the right abstraction of information back.

Here's what's important to us. Hey, watch out this entire other department or this entire business, this existential threat is on our radar. And then that can be translated and filtered down and enriched if you have the right people in place with, local context, local dependencies, local behaviors, local interpersonal considerations.

It's not that you like let go of the reins, it's that you understand what horse you're riding, and how to manage this, kind of growing complexity. You're managing a stable, you're managing a whole farm. You're not managing that one horse to, break a metaphor into bits.

Yaniv: This is a slightly different one because I think sometimes the solution here is if you're worried about becoming this person and you have not been able to keep up with the growth of the organization, one of the things you may need to do is step aside. And this is a very painful thing as a founder.

And to extend the, parenting analogy is it's like, you know what, our little child is all grown up and I'm no longer able to give them the sort of guidance that they need. And they just send them out into the world. Right? And, it's hard, but if you've never managed a large team before, you've founded a startup on day one, and suddenly you're responsible for a 500 person organization, some people can grow into that role fast enough, other people cannot.

And again, the, lesson of all of these archetypes as a founder of it is have self-knowledge, have self-reflection, and get other people to help you If you need with that self-knowledge and self-reflection, but know yourself and then make the right decisions in the interest of the organization and the company.

Know what you want to be, know what you're trying to build.

Chris: But to be clear, right? having a founder step aside is highly undesirable, right? I don't want to give investors, founders, operators the impression that this is a desirable or easy choice. one of the unfair advantages of a startup, a scale up a younger tech company, and when I say younger, I mean Facebook is younger than General Electric, right?

So Facebook is still young in the grand scheme of things, is that the founder is in charge and they can. at the right time, in the right way. Turn an aircraft carrier on a dime and have it act like a speedboat when necessary. And they can influence things to be more agile, be more iterative, be more bold, more brash, and, affect the kind of change that large legacy companies where the founder has died or stepped off are unable to do.

And so it is undesirable to have the founders set aside. So if you're a founder in this position, and it's probably a, small, small portion of our audience, you wanna try to get executive coaches and guides and executives on your team who can help you, mature as fast as possible so that you don't, fall off the wave you yourself have created.

Yaniv: Okay, so archetype number six of seven is the weather vein. So this is the person who kind of changes their mind all the time and tends to reflect the opinion of whoever spoke most compellingly or most recently in their ear.

This is an interesting one and I've, I've seen it quite a few times and as with the helicopter parent, this comes from a founder who doesn't. Invest enough in their own personal growth as a leader, as their company scales up.

Right? So it used to be small, it used to be manageable, The person used to be able to keep it all in their own heads, and they felt a certain sense of authority. Right. And then the company grew and they hired more senior people, often more senior than themselves.

And they hired them in the words of that famous Steve Jobs quote, not to tell them what to do, but so that those people they hired could tell them what to do. But unlike Steve Jobs, they didn't have a strong enough. Sense of who they are and, what they're building. A strong enough vision that they can incorporate the strongly held opinions of their newly hired senior leaders and make that part of a coherent whole.

Instead, what they kind of are is like the weak leader of a clan of warlords, right? Who are each kind of jockeying for their own vision and their own view to be the dominant one. And again, they've hired smart people. They've, hired senior people who are used to being listened to. And so these folks are in the ears of the founder saying, you should do this, and this is why.

And they're making compelling arguments. And the founder in a sense, gets overwhelmed by the, rhetoric or maybe, you sort of the forcefulness of The people who report to them, and they change their mind all the time. And that is very difficult for everybody to work with, for the team to work with because the founder is not charging a course.

They're simply holding up a mirror to whoever they spoke to last. And like I said, to me, this speaks of a type of immaturity. like I said, being a founder is a heavy responsibility. The bigger the organization, the heavier the responsibility, whether you like it or not. And so you need to, as a founder, feel like you have the authority, the gravitas, the vision to represent a view strongly, to incorporate input, to listen to people, but ultimately to share a cohesive worldview that doesn't just constantly change based on what you're hearing.

And if you can't do that again, Chris, of course, You were right when you said that Stepping Aside is a bit of a last resort, but you should be investing in yourself so that you never get to that stage. And there are a lot of resources available for that.

Chris: As you were talking, I was reminded again, that this advice that we talk about is often so hard to parse because it's all a matter of degrees and it's all a matter of, knowing which advice to apply at what time, and it can feel very contradictory, right?

In the last few archetypes we've been talking about not trusting your team enough now we're talking about, not listening to your team too much and, leading it with a common and cohesive worldview. we've talked about being flexible and adaptable and agile, but you don't want to be too adaptable and too flexible, too agile.

And so all of these things are really about degrees and it's about knowing. When and how to apply the right thing at the right time. you also talked a lot about internal influence, right? Your executives jockeying for power and, the founder being a bit of a weather, va.

Of course, this is also connected to the deals, deals deals. sex addict archetype who, they talk to in in the market, the last deal, the last person they speak to, they're like, yeah, let's go do that. That's the future of the business. And so they're a bit of a weather vein in terms of, what they should be building and what the customer is asking for.

Yaniv: I feel there's a, lesson that we've talked about that's worth drawing out a bit more, that sort of then feeds into our seventh archetype, which to your point Chris, is a bit of a meta archetype. And the lesson here is actually to avoid becoming one of these founders.

Sometimes say it's, difficult to read the label from inside the bubble. You absolutely need to get better at self-reflection and thinking about how you are leading the organization and what you need to do to get better and so on. the truth is, the best way to make sure that you're not falling into any of these archetypes is to hear from other people, to get feedback from your team, from those around you, from your investors, from mentors, perhaps from an advisory board.

We talked about that in a recent episode from an executive coach. listen to people around you, right? The, fundamental skill of a founder, if we really wanted to abstract it, is one of learning and growth, because as a founder, no founder knows all of it, really, nobody starting any company, even a repeat founder, but definitely a first time founder has all the skills and all the capabilities to be able to do their job effectively at the beginning.

They need to be constantly learning and growing. And so that needs to nearly be a big part of the job that you see for yourself is not just building the thing that builds the thing, but in a sense, building the thing that builds the thing that builds the thing.

And first thing, that's you. That's yourself as a leader, right? You need to be investing in yourself. It's not selfish. It's not distracting you from the main job because God willing, your company gets to a point where it's gonna demand more from you than you're currently able to give, and you better be there, ready and waiting to meet it when it gets there.

Chris: It's so true that no founder obviously is born an incredible founder. Every new business that you start requires different things from you and the company. And so some of your muscle memory may not apply even if you've been successful before. And even then, as you say, you can't read the label from inside the bottle.

I like that metaphor and that suggests also that even if you're an incredible founder, you're an incredible multi-time founder, you know this domain very well, you still may be too much in the weeds, too close to the problem to really see the full picture.

And so in all of those cases, having one or two or three people that you really trust who are perhaps outside of the company because they don't have horse in the race, who can give you some clear and concise advice, and help restore that perspective for you.

I'll often find myself giving advice to founders. Who I will later realize that I myself am not following for things that I am working on myself. And that's because I'm inside the bottle. And then I'm like, holy shit, Chris. you talk about this all the time, why is it so hard to see it for yourself?

And it's, not because I'm a hypocrite. It's not because I'm making this stuff up. It's because I'm in the weeds of my own problems.

Yaniv: You're human.

Chris: I'm human. Yeah. And, I'm often fond of telling the founders that I'm working with. Some of my advice is, because I've done this before, some of this advice is because I'm, yeah, I'm clever at this particular domain.

And some of this advice, or a lot of this advice is just because I have emotional and tactical distance from the problem. And I'm like a drone hovering above the forest, and I can tell you which way is north. and you are kind of stuck looking at the trees. And so it, is really for an advisor, for a coach, for somebody who's helping you out, it's really a giant cheat code.

So you want someone who's experienced, you want someone who's clever, but you want someone who has emotional and tactical distance from the business. their part timeness, their fractional is not a bug, it's a feature. and so really pay attention to that.

Yaniv: You know, who tries to be a founder all on their own idiots. That's who it's a really bad idea.

You are not going to have the self knowledge, the insight, the reflection to do the job well, to avoid all of these archetypes, which like I said, these are not broken people, these are not people with personality disorders. Any of us could become any of these things if we're not careful, if we're not learning, if we're not growing, if we're not reflecting, if we're not course correcting based on feedback and based on a really nuanced understanding of the situation.

So please, the lesson that we would like you to take about this, like I said, it's an EDU episode. We want you to avoid these pitfalls, get help from people and listen to them. Now, we're actually not at the end of this episode because there is one final archetype, and Chris, this is your one.

So we call this the Memento guy. Tell us about the memento.

Chris: That's right. If you haven't seen, Christopher Nolan's incredible movie called Memento, you need to see it. But, minor spoilers 'cause you learn this very quickly. he has a kind of weird form of amnesia where he can't make new memories. the memento guy. Or girl or person, is experiencing one or more of these archetypal problems or maybe something else, and reaches a new consensus with their advisors, their mentors, their executives, the market, what have you.

But very quickly, the next day, the next week kind of slips back to their previous muscle memory, their previous thinking about the problem or situation. And so they might come to a new consensus like, yeah, you're right. I'm too involved in the details and I'm gonna step back from that. And then next week it's like, no, no, no.

Need to be involved in these details. Let me back into the details. Or you're right, we're too focused on sales and we're too obsessed with, revenue. We need to go switch to a more scale based, methodology and go to market strategy and then next week it's like, no, no, you don't understand. We need this revenue and it's just impossible.

And where there's just no way to throw the needle. And it's just like, dude, we talked about this last week. so you need to be careful about being the founder who has these moments of, clarity. And then lets the world wash over them and, collapse them back down to their safe place.

Their default position.

Yaniv: So, the reason we had that little rant about learning and growing, before this one, Chris, is because this is really about a failure to learn and grow. It's about being stuck in what you are and not adapting to the situation. And it can be incredibly frustrating for those around a founder like that because they think they're making progress, but the person snaps back, they wake up every morning, you call it Memento, you call it Groundhog Day.

It's, part of that same type of, whatever cultural reference you like. They come back in, it's a new day. It's a new week, and it's like all of that feedback, all of that personal growth has been rewound, and we're starting again. And, eventually what that will do is, first of all, it allows all the other dysfunctions to creep in, right?

That's why we call it a sort of a meta archetype. but it will also massively frustrate the people around you. And, and it will cause people to eventually give up on you. And that's the most dangerous thing, right? It's like if, a person is not good at taking feedback and input and growing and changing how they do things, and eventually those around them will stop trying, and then the founder is truly isolated, Then they're just, a bit of a liability to be managed and to be humid so that they don't do too much harm to the rest of the organization. And apart from the impact that has on the business, I think it's tragic. imagine that being you, imagine being a founder who's showing up every day.

Really cares about their startup, really cares about their business is working hard. By the way. This is not about slacking off, and yet people are just like, oh, you know, this person's stuck in their own habits. Let's just try to keep them out of the way so we can get actual shit done. it's a bit of a tragedy and so I think having, that growth mindset and that willingness to really want to change because we're all going to need to change on this journey, I think that is really the most important part of everything that we've talked about.

Chris: as we like to do yev, I think we often pull out these kind of meta, themes or meta insights at the end of some of these episodes. And I think startups are really about growth. And adaptation, and accountability. and so so what we're talking about here at the end is applying those same principles to yourself.

You need to grow as fast as your startup is. You need to be able to adapt to what your startup needs you to be and understand how to thread that needle from being a weather vane or too changeable, but adapting in the right way. And you need to hold yourself accountable. You need to, make the changes that improve yourself, improve the builder.

As you said, Yaniv improved. The builder that builds the thing. That builds the thing. and so, these things apply to startups in general. When I talk about accountability, it's like sell your own shit. And, you know, adaptability as it needs to be an agile, iterative process and growth, you need to focus on getting that hockey stick growth, right?

The same. Principles apply to the people running the company. and I think that's, the meta theme here.

Yaniv: That is indeed the meta theme, folks, if you want someone who can help you with that little bit of distance, giving you that feedback on how you're running the organization.

Chris, you're not an executive coach, but you're giving feedback that very much. Goes into the types of behaviors and the way that people work. so if you wanna add a really great fractional executive, such as Chris, to your wider circle, Chris, I know this is something you do. How do people get in touch with

Chris: Yeah, that's right. And you know, a lot of these. Archetypes we've been talking about are based on my experience with founders and with leaders in companies and, you see these kind of, patterns and behaviors a lot. And I spend a lot of my time in my advisory work helping people to identify these patterns, but more importantly, to break out of them and to hold themselves accountable.

And so if you wanna learn more about that, check out chris ard.com/advisory and you can, reach out from there.

Yaniv: Okay, Chris, thanks for that and thanks for a really great episode. I enjoyed it. Folks, just another reminder, please join our mailing list at TSP Show. Just enter your email address and you will get all the latest from us, episode reminders, exclusive content, and more. thanks very much for listening and see you

next week.

Chris: See you all next week. Bye-bye.