Startup Therapy Podcast

Episode #7


Ryan Rutan: Hey, this is Ryan Rutan from startups dot com back for another episode of the startup therapy podcast with my partner and co host Wil schroder. Well at the risk of sounding like I'm shamelessly building you up. I'm going to rattle off a bunch of your accomplishments and now

Wil Schroter: you can pretend you can pretend you're embarrassed

Ryan Rutan: if you want. I'll know the truth. But at the end there is a twist. So you've started nine companies, you've sold three of them. Blue Diesel got cast unsubscribe dot com. You've raised money from places like founders fund 500 startups. Mark Suster first round capital, You've been a founder for 25 years. You started your first company at 19 blue diesel, which grew to $700 million. Um, 650 people 10 million a month in payroll, which then you know, went on after a couple of trades to be a $3 billion startups.com, million dollars valuation. We bought six companies along the way. Fun doubles hit 500 million in capital raised launch rock has helped 500,000 companies launch we got more than 20,000 mentors on clarity and on startups.com as a platform. We have over a million users now, conspicuously missing from this list and pertinent to today's conversation is a college degree.

Wil Schroter: I want to

Ryan Rutan: know, I want to know. How often do you look at that empty spot on your office wall and wish there was framed proof of putting up with somebody else's bullshit for four years. I mean, a college

Wil Schroter: Degree. I remember. Well, first off, exactly. Never. Okay, good. 2nd off. I mean, man, I remember in 94 95 going to my college and I was in college at the time going to my college guidance counselor. I remember I was sitting across, we're so excited and I said to her, I said, look, I am dropping out of college right now. Normally that's followed up by somebody talking about how, you know, the family problems or they're they're failing out of college. I was basically looking for a high five to tell her how excited I was to drop out of college. She looked at me like incredulously like,

Ryan Rutan: I'm guessing her expectations fell short.

Wil Schroter: Oh God, yeah. And and she and she looked at me like, I, I don't understand like you, it sounds like you're telling me you want to drop out of college. I said, yeah. I said, I'm starting an internet company. And I remember, I'll never forget. She said that she looked at me dead in the eye and she says, what's the internet? Yeah, There was a time, right? I mean, there was a time when, you know, no one knew what the hell the internet was. And I just remember thinking to myself, damn, she's right, Maybe this isn't such a good idea. And it was it was such a important kind of monumental moment to me because I was so convinced that I could go start something, This internet thing, you know, it's one of the first web design companies, but you know, who knew back then. But it didn't occur to me at the time that I actually didn't know what I was doing right. Like I had no credentials for, for this new career whatsoever. And at a time, you know, people forget about this, but at a time when there was wasn't any precedent For being a 19 year old person starting an Internet company. Now, it's passe, it's almost like if you're not 19 starting Internet company,

Ryan Rutan: Right? But I'm looking at your resume here and it looks like between the ages of 16 and 21 you didn't, you didn't found anything. So why are we talking?

Wil Schroter: What a slacker. Right. But what was interesting to me was it was an era where um you were used to seeing the pasty faced guy on the cover of Forbes that was, you know, graying at the temples, talking about being the young ceo of a new company. Right? And here I was also pasty faced except where a beard would be. I had a bunch of pimples. And what was interesting to me is for that moment, it didn't occur to me yet how massively under qualified I was to go on the journey I was about to go on, right? Because you know, I didn't have any experience. I was a theater major, I mean I wasn't even interested in business.

Ryan Rutan: Well when you don't know what you're doing, having a background in the theater can come in handy when

Wil Schroter: it did come in handy because I was faking it for a very long time and I was basically acting my entire way, who knows? Maybe I still am. But if I jump into this company start Blue Diesel in short order, like any other founder, I realized how woefully over my toes I am. And so at that moment and I think this is common for founders at that moment I felt like there was someone else, some Yoda guru that had all the answers to this thing called business. And if I could just one day get their experience or go through the Jedi trials or whatever the hell you had to do to become the dude that was on the cover of Forbes, that I would then have the ability to become a Ceo to be a founder. And for a long time I held that belief and this is kind of the genesis of all of this. Years later, the company starts growing exponentially fast. We were really fortunate. We want some big accounts, things did really well and fast forward about six years later And I'm 25 at the time and I'll never forget by that point, the company had grown quite a bit, but at that point I remember looking around going, you know, it's been six years at this point, I haven't, you know I haven't gotten a degree, I've got an M. B. A. I've done all any of the things that people expect someone to do in order to kind of earn their way into that job and I'm doing a pretty good job like things are going pretty well like you know what I mean? The company's growing like crazy. I seem to be hiring people, we seem to be making money, we seem to be winning clients. I seem to be doing all the things that a ceo does and technically I'm not qualified whatsoever. It was at that moment that I realized that my age wasn't really my delimit er now I had some experience I needed to get But I was just as capable at 25 years old as I was going to be for the rest of my life. And at that point like everything changed for me, how I looked at that talent, how I looked at myself and it was the first time. It really it really occurred to me that the degree that the level of experience, not that it didn't matter, it didn't choose my future.

Ryan Rutan: Well you were also in an industry at the time that was largely undefined. There wasn't anybody who had a ton of experience and and really the nature of a lot of what we do in startups is under conditions of extreme uncertainty where there isn't a precedent. And so I think that to boil down some of what you were just talking about is to say that there's a bit of a difference between experience which helps you to shortcut things that you know, you need to do and just raw processing power, which is to say I can figure stuff out and We don't tend to get better at just figuring stuff out as as we get older right? Like to your point, I think like you're probably as capable more capable of just gutting through things at 19 as as we are in our 40s,

Wil Schroter: right? And where I where I think that started to become a big challenge for me was I had this blatant insecurity that because I was so young and I just assumed everybody that was much older than me kind of had all the answers and by way of that they were more capable. I started to project that insecurity across my entire staff, right? So I would look at somebody that was a year out of college and I would think, well I know I didn't know anything and I wasn't capable, so I guess they're not capable to and so I relegated them to roles and jobs that were specific to what I deemed their level of responsibility and to be clear, so does the entire rest of the world,

Ryan Rutan: the normal career progression, right? That's the rubric we use to measure people, what have you already done? How long have you been doing it? Okay, That tells me what you can do today. Which, which is dangerous,

Wil Schroter: and I don't think it's accurate right now. Again, if we are to separate two really critical attributes, if you will on the left side, we've got your raw talent, your creativity, your I. Q. Your ability to communicate again. Just those raw, innate talents on the right side, You've got your experience, just some shit. You don't know yet, right? You know, you have never forecasted the financials of a company. You just don't know that, right? What I think tends to happen is we tie those two together, right? We say that if you don't have the experience, then that delimit your raw capability, right? And what I was learning to do was separate the two to say here are the reasons I can't move forward because of experience, and here are the reasons I can't move forward from rock capability.

Ryan Rutan: There's a bit of a reverse of the peter principle here, right? Which is to say that, you know, you tend to get promoted to your highest level of incompetence. And this is saying that we're, we're arbitrarily slowing people down because we're waiting for them to prove that they're capable of at the stage that they're already at.

Wil Schroter: We're also doing the opposite. Arbitrarily giving people credit for things they haven't done yet. Ergo I went to this college, I earned that degree awesome. Have you done it yet? Right?

Ryan Rutan: Like, like

Wil Schroter: I've written books on Photoshop, I'm not very good at it. I've taken courses on photography. I'm not very good at it, right? Just because I learned it, it's not the same as me being good at it.

Ryan Rutan: Yeah, nor nor do you need that credential to prove that you're good at it, which I think is where we get into the meritocracy. That is the startup space,

Wil Schroter: which is incredible to me and and it's something I know that we've made the core of our fabric at startups dot com and Ryan, you and I and a lot of even the other senior managers on paper, our resumes don't qualify us to do these jobs, right?

Ryan Rutan: Well I've tried to destroy every, every copy of my resume that have ever existed so that nobody can verify exactly that fact.

Wil Schroter: You know, and and, and and what's fascinating to me is we've got this weird dichotomy where we're saying if someone has these prefabricated degrees, this, this this track, then they must be qualified to be good at their job, right? And I really want to distinguish those two facts. There's a difference between saying I have the, the education and the experience to be able to do this job and then there's another one to say that I'm actually good at it, right? And and I haven't seen a strong correlation between those two, right? I've seen more success and maybe it's because I'm surprised by it from folks that don't have the innate credentials but have so much hustle and so much ambition and so much creativity that they just kill it at their jobs.

Ryan Rutan: Yeah. You know, it's to me it's it's less about where you've been, i e the timeline of your career and what you did while you were there if you went to college, Great. But talk to me about like what happened while you were there and if the answer is I took classes

Wil Schroter: and I

Ryan Rutan: got it, I got a degree and I'm a marketer, right? And that's that that tells that does tell me everything I need to know. Which is that uh we should finish lunch as quickly as we can and I should never talk to you again. Whereas, you know, I talked to somebody who's a bit more of a hustle and I said, well, you know, yeah I was in college Um you know, my my G. P. A. was only a 2.9, I was spending most of my time on this other thing that was super interested in. And here's what I did with it like that tells me that put into a situation and given some resources this person has the ability to figure sh it out and do things right. They may not have been that the things they were supposed to be doing at the time per the kind of metrics of college, but it still shows me some initiatives, some ability to take resources and do something with them that's far more indicative of this is somebody I want to hire, somebody want to work with somebody at least wanna play test. Then I had a four point oh and I was the captain of the debate team and all these other accolades that people stack up as if that tells me anything, anything at all about their capability within a job,

Wil Schroter: right? And I really try to separate what have you learned from? What have you done? Right? And I'm not discounting learning learning is valuable, right? The experience is valuable, but it's not the same as what you've done.

Ryan Rutan: It's not right, It's not and it's not valuable at all if you haven't applied it because that's often the step that ends up being the one that people trip over there. Like I've learned everything about this topic and then the minute you go to apply it, it just falls apart. That's where truly rubber meets the

Wil Schroter: road and that's where, that's where the merit comes in, right? So I sometimes feel a little bit of entitlement. We have someone come in the interview and they'll come from a top school and they'll say, you know, I, I graduated this program this school and so therefore I deserve, you know, a great job and I keep scratching my head going. I in all of my years have I run into somebody where what they've said is I know the answer. I learned it in college, right? Like, like all of the practical application, knowledge that I've yet to see has all come from real world experience and this isn't me knocking college right? I just want to be clear. I'm separating the two. College is wonderful and the experience is wonderful. So long as it doesn't present an entitlement to be the same as, and this is what I accomplished,

Ryan Rutan: right? I I went through that, therefore I have earned X, Y or Z, right? That's that's that's not what it's about.

Wil Schroter: It's, it's when, when, when a creative comes to me and says, well, I went to art school and we learned this like, fun, who cares? Like show me

Ryan Rutan: your portfolio. Well, it's not really indicative of who I am as an artist at this point in my life, because you know, that was under some just go away. Please just go away. Yeah.

Wil Schroter: Like, man, I don't care how many times you've been in practice. If you can't score points in the game, you're not an athlete, you don't get to play, right. And, and

Ryan Rutan: so my dad used to say that, right, practice makes permanent, not perfect practice makes perfect, you're practicing something the wrong way. And college is pretty good at that in a lot of ways. It's like, hey, let's teach you one of several various outmoded ways of doing something just by the nature of how academia works. That's the way it happens doesn't make you perfect. It makes you permanent. You learn something. And again when it comes to applying that it becomes really tough right? Like if we're trying to hire developers right out of college who had never done anything but their college courses the vast majority of them would fall well short of the mark of what we need people to be able to do because they weren't taught on the platforms that we use. They weren't taught scenarios that we see in real life right? They were they were coding the hello World stuff and it just isn't applicable to what actually happens your first day on the job.

Wil Schroter: Absolutely and you often weren't doing things with consequences. You're maybe getting graded on it and that has you know kind of a contextual consequence to academia but it ain't the same as if we don't launch this and we don't make money on this we don't get to eat right and those are real consequences right? People

Ryan Rutan: try that. Your G. P. A. Should be directly linked to your meal plan

Wil Schroter: I think mine was. But let me build on that because this isn't just about college right? And again all of this is coming back to the founder and how how how the the founder of the founding team views both itself and its capabilities and its entitlements as well as the staff but it's it's not specific just to college. I'll give you another example come from the other direction, not just the young person coming out of college. The older person coming out of corporate America coming out of big job, right? Coming to your startup in saying I was such, such and such at my old company. Therefore, I know bullshit man, You were the senior vice president at another company, right at that job with those conditions, with those clients, with that team, with that real budget. We're still sitting on cardboard boxes, right? Like your experience there while helpful isn't the same as your entitlement here. You kinda have to earn your entitlement here.

Ryan Rutan: Sure. So that's, that's interesting. So there's this sort of dual challenge in that if you don't have much of a history, don't try to use what little history you have to dictate your future. But in the same way, even if you have a long trajectory and a long career doesn't necessarily mean you can, you can do that either. Right? And you've, you've written about this before will and you said, you know, hard to get people to stop thinking about their past as the deal emitter of their future, whether that's through a lot of experience or through a little experience, it's dangerous to use that as the vector for the future,

Wil Schroter: right? And, and, and, and, and again, I keep coming back to this concept of entitlement whereby again, we're going to use an older executive, which oddly means older being you and I now rent, but an older executive kind of, you know, a bunch of relics But older and older executive kind of coming into the company and saying I've been selling them for 20 years like dude, who cares right are you selling now? Right? Like I don't like this idea that people can use their, their, their badge of honor to say what I've done in the past automatically entitles me to a certain treatment or a certain expectation for the future because often people are kind of resting on laurels or resting on a career that's just not relevant anymore.

Ryan Rutan: Yeah, it's, it's as if when people come through the door, they forget that the reason for presenting these accomplishments history accolades is to give the hiring manager whether that's the Ceo or or somebody in middle management, whoever is going to be making the decision on this individual some shortcuts to understanding whether this person is right for the role or not. It's not a matter of, well, I've, I've checked all the boxes so therefore I'm hired. Right? Well, that decision is still up to us. And so it always surprises me how little people do to try to contextualize their experience into our situation. You know, if you can at least draw those lines right? Say because I did this, it's relevant to what you're doing in this way, not just like, well, you know, I, I lead a sales team and I was, I was, you know, routinely in the top three. Okay, cool. Like what makes you think you'll be able to do that here? How were you supportive? What was it that you did to drive that outcome? Not just that you were involved in a team that won, right? It's like saying like I have a super bowl ring, what did you do Ryan? I was a statistician right after that's not important. But like you don't want, if I'm applying to throw a football, you might want to know that little detail about me that I've never thrown the football, but I was on the winning

Wil Schroter: team. I think in both cases, whether it's more senior person, more junior person coming into the org, what we've learned and I think what we've excelled at at startups dot com and with our team and it's been a lot of trial and error. I mean we have a lot of hit or miss over the years, but I think what's, what I'm finding is working really well for us is we're giving people far more responsibility than their past or their, their resume has entitled them to and we're judging them on what happens when we kind of over accelerate a bit right. We're saying if you're as good as you think you are, here's two X the responsibility, not even the workload, but two X the responsibility. There is an archetype of the person we're looking for that. Well, grab onto that and get so excited about it right? Maybe get a little overwhelmed but that's okay right. There's there's a certain type of person that I think is made for startups that appreciates jumping into the deep end, right in learning how to swim that way. And I think when you limit people in their responsibility to just what you think their experience level entitles them to now, I I feel like you don't get a chance to test that metal if that makes

Ryan Rutan: that's exactly it. No, no it's exactly, I mean I go back to go back to the exercise we used to do in kindergarten stretch and grow right, we all started the day that way and that's exactly what it takes if you aren't given the opportunity or even having the opportunity of foisted on you in terms of responsibility to stretch those capability boundaries, whether they're real or perceived, you're not going to have a chance to grow. And so I think that it is one of the most important things that we can do for our team, anybody can do for the team is to make sure that they're in a situation where they have that room to run, you know, with some guidelines with some rails on it. But if they're not given the opportunity to stretch out and grow, they're not going to, there's no version of I keep doing the exact same thing over and over and somehow that adds up to leveling up into the next role or the next level responsibility. That's just not how it works. You don't get the ability to handle the next level until you start taking on the next level in reality.

Wil Schroter: And I see the opposite. Like I see a case where most founders Actually feel the opposite way that they feel like they're not capable enough, right? They feel like, well I'm not ready for this job. I'm 24 years old and how could I be possibly experienced enough for this role as a ceo and in all fairness, you actually may not be right. You're probably not experienced enough. No one ever is, no one's ever experienced enough to be the founder. That's like being experienced enough to be the president and nobody is, it's, it's too complicated of a job, right to say I'm not capable of doing it. Well, that's when I, when I separated those two things. When Ryan, when you and I talked about the idea of capability on one side and experience on the other, How do you know, you're not capable enough, you know, capable is going to be I q creativity, all these different stats. Have you really tested it right? Like I have you given yourself enough time, you'll definitely find more experienced people if you're earlier in your career. That doesn't necessarily, you're going to find more capable people and I think that's a massive difference and how we think about kind of this, this concept of Am I ready? Am I entitled, etcetera?

Ryan Rutan: Sure. And I'm sure the mileage varies and a roll to roll depending on how valuable experiences. But if you're gonna end up doing the same thing day in day out, experience ends up being very valuable because it will teach you optimized ways of doing that. It will teach you how to be very efficient in the role backing up on what you said when you're inexperienced, but you're facing situations that you wouldn't have ever had a chance to experience. And sometimes you never will. Again, it isn't about having the appropriate experience to handle that challenge. It's about how you handle the things that you have never faced before, right? And that I think is a hallmark of true leadership is the ability to react. And unfortunately, there isn't, there aren't a lot of great tests to prove that out before the fact, but I think that's a great reminder that at all levels of work, there's some level of leadership required, that's just leading yourself through your day and getting your task work done. And so I think we need to give people that room that freedom again to to run and test those limits and to make sure that, you know, we have enough shots on goal with them to see how do they react when, when things aren't exactly certain things aren't prescribed for them and it's never going to be easy to measure. But there isn't really a great way of assessing that before. The

Wil Schroter: fact, I also don't think any, every founder Ceo or founding team Is necessarily ready to let other people run as fast as they can run, right again, because they may have been brought up on this, this linear thinking that, Hey, I'm, I'm 25 years old in my career. Therefore I've been told by my dad, my mom and everybody else that until I hit 35-45, I'm not ready for senior leadership. If, if that's your mentality and I'm going to point out how I think that is largely flawed thinking. If that's your mentality, how you feel about your own career, you're then going to propagate that to all the people that report to you and you're going to deliver their opportunities because of your own prejudice, which

Ryan Rutan: we have a rule, we have a rule in this country that says, you can't be the president until you're a certain age, Right? So we, we, we have definitely adopted this, uh, this, this ideology that, you know, with age and experience comes capability. And to your point, I think it's, I think it's time we break that down a bit and really think about how we're thinking about these things.

Wil Schroter: And I found this wonderful exercise again and, and folks and all ends of the experience spectrum whereby when you give someone a task or a project that's open ended, where it doesn't have a prescriptive outcome, in other words, you say get us two x more customers or you say invent the product that we're going to work on next more than anything that tends to separate the people who are truly self motivated and have that kind of their own level of ambition from the folks that are just order takers. And they're just kind of like churning through these very linear kind of this is exactly my job type roles. And I've seen the shining examples of people who just kick asset, their job that are far more capable than their experience or resume would tell you consistently performing on open ended tasks.

Ryan Rutan: Now, I agree with you. Let me start by saying that. But now I want to play Devil's Advocate just a little bit and ask what happens, when is there a line. Do you think there's a line that you can cross between giving people open ended assignments and giving them flexibility and people feeling like there's not enough direction from leadership and where do you think that line exists?

Wil Schroter: Oh boy, Considering people usually point the finger at you when they're saying that, I think it exists a lot, you know, and I think it's it's a valid question.

Ryan Rutan: A

Wil Schroter: very backhanded way of asking me a very specific question. Now, uh, I think, yes, you can give somebody, you know, so much running room that you let them run off a cliff. Right? And so, so I think, you know, some appropriate parameters should exist however, and I don't know, maybe this is maybe it's just my personal style, but I feel like the folks I'm looking for want as much running room as they can get right, like I

Ryan Rutan: agree, I agree with that too.

Wil Schroter: And what we've seen, you know, we've got some extremely young members on our executive team, right? You know, his

Ryan Rutan: youngest,

Wil Schroter: yeah, not you, you know like our, our youngest members in, in his early twenties and the oldest is some guy in his forties and so

Ryan Rutan: yeah,

Wil Schroter: yeah. And so, um, you know, a fairly, fairly significant age gap. But the folks that are there on the executive team that are younger all have one thing in common. They all perform best when all the parameters are taken off. They also perform best when we never think about how much experience they don't have because literally we're talking about when assigning a task, All we think about is, here's the task. We think this person has a tremendous amount of capability to burn through it. Let's just drop it on them and let them run and you know what and Ryan, we've been at this a long time. We've tried this with people of all different experience levels. It consistently breaks for the wrong people.

Ryan Rutan: I think what you're saying is that it breaks in the right cases, which is to say that like it when it tells us what we need to know about somebody.

Wil Schroter: Yeah. And

Ryan Rutan: and and when they're the wrong person for the role, it breaks them or the process breaks down, right.

Wil Schroter: And what we're saying is you can move as fast as you want in the organization so long as you run at your speed at the fastest version of your speed. In other words, if I say you're 22 years old, you're coming out with with a marketing degree from X University. I don't even care what the university is and you're saying that you want to lead paid acquisition for the company. Okay, That's interesting. You've never really done it in a meaningful way. You did a couple internships where you played around with it. I'll give you a task, here's a certain amount of budget, here is a specific acquisition goal. Go make that happen. What I'd prefer you didn't do it if you didn't have to do is come back to me with the answer with questions to the answer to every part of the test, right, google it, figure it out right? But the right person, they don't want to come back to you and and and be handheld. They want to go figure it out for themselves and more importantly, they want to crush that number, yep. And random

Ryan Rutan: directions, hand them the direction to go in, right hand them the outcome that you're after hand them the objectives that you want them to reach, give them the freedom to do that and then we want to come back. Aren't more questions we want we want outcomes to come back. I want to see the results at that point

Wil Schroter: and I think one more,

Ryan Rutan: there's one more piece of devil's advocacy and me over this over this concept and one that one that I've had some struggles with in the past and this predates startups dot com. But it's this notion that when you're giving individuals freedom of how to accomplish their goals the time in which to do it, the methodology that gets them there in a vacuum on a single path, I think that it's, it's very easy to see the benefits where I personally have seen this breakdown a bit, is when you start to do this organization wide, you start to lose a little bit of cohesion unit to unit or team member of a team member and this can throw things into a bit of a, a stressful situation for everybody involved, whereby you've got some dependencies, right? If if work was completely independent of what I did was completely independent from what you do or completely independent from Elliott does or anybody else on the team. I think that there there's no issue with this, but to the extent that were inextricably linked in the outcomes that we're trying to drive and sometimes there are strong dependencies on these. Let me let me give an example, Elliot would come to me, Let's just go back five or six years in time. Say, Hey Ryan, I've got this idea for, for a new product that I want this sales team to, to be able to offer to our audience and here's what it is and say, okay, cool. Probably give me about a month to be able to deliver on that. He's like, okay, cool, we're gonna start selling it tomorrow. Right? So there's like this, there's this like we both have our objective, we both have the freedom to go and figure out what we want to do. But when the timelines or maybe even the directionality outcome becomes incongruent, how do you balance that? How do you make sure when you're sitting on the top of this thing is the founder, that, that there's some balance there so that everything kind of keeps moving together.

Wil Schroter: Well, here's where I think it's even trickier than that. Every time I say, go do something you've never done before. I'm also running the risk that you won't actually get it done alright. You know, if I say, I need to know that was an option. Yeah, Well it's been proven that that can actually happen. You know, if I say here, I want you to run the four minute mile. That's cool. Unless you don't do it right in all of this, Hey, let's, let's create a meritocracy. It's, it's highly based on the fact that people are actually following through with these big opportunities. I just want to be clear and I'll tie this back to what you're saying. Most people fail at this, right? This isn't, this isn't the case where where this amazing meritocracy and everyone gets an opportunity and everyone crushes it, everyone doesn't crush it, most people fail, right? So when we're talking about all of these parallel initiatives, like you're talking about like things you would run with Elliott et cetera and we're talking about, are they congruent with each other? I think part of the bigger challenge you start to run into is sometimes they're not congruent because people are running kind of their own path, going their own direction, but at the same time you're often taking people way out of their comfort zone and inviting a tremendous amount of failure and I don't know that a lot of ceos or a lot of managers kind of have that luxury, hey, I'd love to give people more opportunity, but I kinda can't afford for you to follow this up.

Ryan Rutan: Sure, sure, Yeah. And that's, that's where the, you know, I think setting the objective and realistic milestones really becomes important because, and you just said this, but opportunity does not necessarily mean success opportunity means absolutely, you've got the, the chance to do something right? There's, there's a big difference between opportunity and actually exercising that, that opportunity. Speaking of exercise right there, there's no shortage of gyms in this country. So there's plenty of opportunity to work out. And yet when I look around, it seems that there's a lot of people who aren't living up to their opportunity to the potential of the opportunity, right?

Wil Schroter: Agreed. And, and, and also to be fair, there's a big delta between when people say I want more responsibility, I want more opportunity in them actually meaning that, right? So often people will come to us and say, man like, you know, how can I advance? I want to be able to do more and there's always this little voice in the vacuum that are saying, do you right? Because that's really hard, right? Like you know what they're really saying is I want to be given more responsibility often more compensation. Uh, you know, I want to get paid more. Yeah, yeah, I want the payment part up. You know, like I, I'm a little fuzzy on, on the whole have to work more, right? Or

Ryan Rutan: I'd like you to, I'd like to explain to me how we can de risk my next salary. Like for me specifically.

Wil Schroter: Well, and, and, and so it's, it's, it's not that people aren't willing to put in some more effort. It's often they don't realize that they're not capable of what that next level is like, well, hey, give me a shot, you know, I want a shot at management. It's like dude management isn't a walk on position. Like, like management assumes that you've proven that you can make lots of good decisions, anybody can tell other people what to do, getting them to do things when they don't want to write or aren't capable or getting out of a shitty situation. That's management, right? Doing performance reviews and assigning tasks. That's just administrative, Right? It's, it's so when people say, hey, you know, I want this next opportunity, again, it often involves management, etcetera. It's a risk on behalf of the organization to give them that opportunity because there's a real cost if they get it wrong, right? And so, so when when we're trying to create this meritocracy within the company were trying to say, we want to push you harder, We want to take you out of your comfort zone in a good way. But we also have to be mindful of the cost to the organization when we go to do it.

Ryan Rutan: Sure. Yeah. And you know, it's, it's the, this is the peter principle, right? Which is to say that you've now promoted somebody into a position that they are least likely to succeed in, or less likely to succeed and then they were, or less capable of succeeding than they were in the prior role. But so how do we, how do we balance that against what we've been saying this entire time, which is that experience and, and track record aren't indicative of your ability. Do you feel like there's there's a difference in the way that gets interpreted when it's time to talk about being a manager as opposed to being a player?

Wil Schroter: Yeah, I think I think what we've done well is we've said, look, you've got two or three initiative two or three projects that you're working on. One of them is a bit of a Moonshot, right? One of them is a you're really on this to see if you can do more than you normally do? Yeah. There to have to get done and they're well within your wheelhouse, right? And we've seen time and time again that the right person will just crush it at the Moonshot project and earn their spot on the team, right again, regardless of where they came from. You know, whether they had more experience less experience the right archetype that we're looking for, wants that increased responsibility, wants to move out of their comfort zone, and they're really kind of glom onto the project that allows them to get them they're the wrong person when given the increased responsibility and the opportunity to kind of earn their spot on their team will say, well, tell me exactly how to do it, Tell me exactly how to not get it wrong and kind of hand hold me through that process, right? Well, we could, but if we had to hand hold you, we just hire somebody who already knew the answer.

Ryan Rutan: Sure. So we've talked a lot about handing people, opportunity, opportunity being given freedom being given, what control does the individual happen all this, how how much capability or ability do they have in setting their own path? Right. What what can people do in the context of a career, whether you're sitting at the helm as a Ceo or a founder or you're within the organization, what's the best way to support this type of Meritocracy and Growth Within 1?

Wil Schroter: You gotta ask for stuff that's beyond your capability. It's it's just that simple, right? And I would say there's there's a few levels of how you can do that because everyone's gonna have their own different situation within a company at present, at the very least at a baseline, you've got to be willing to go to your manager, assuming, you know, you're an employee in the company and say I want to do more, where can I step up? Right now, If you say to a manager, where can I step up and he or she does not have an answer to that question, don't deserve to be a manager, but that notwithstanding, sometimes there aren't more opportunities just to be clear. Sometimes, you know, if somebody's working um, at the cashier at Mcdonald's and goes to their manager and says, how can I do more? It's like, well, you're sort of a cashier right now, a good manager would say, well, let me explain to you, like, you know, how you can be great at this job to get to the next level. But I'm just pointing out that there isn't always an opportunity.

Ryan Rutan: Hold on that point. Hold on that point for just a 2nd 1st, which is be really good at this job first. Right. So I think that one of the challenges that that I've routinely encountered over the years is that people will come and ask me like, what do I have to do to get to the next level? Which again, often means like more calm, more responsibility, a different role. Sometimes it's vertical, sometimes horizontal. Like how do I go and do this instead of saying like, have you fully kicked the ship out of your current role? Because to me that's always an indicator doesn't mean that you're going to stay there, but it means that, you know, you've done what was asked of you, you've gone beyond what was asked of you to your point. They always need to reach a little bit. But I think that reach needs to be predicated on having done as much as they can within the current role and expanding the current role and then reaching for the next one. Nothing is quite as aggravating to me as somebody who if you were just to ask me in a vacuum, like how is that person performing that? They'd be somewhere anywhere below the a the A level I'd be saying like, you know, why are they asking this question? They're not performed in the current role. They want to know what's next. Why aren't they worried about like killing this one? This is where you are now. Do as much as you can hear first, then let's talk about what happens next.

Wil Schroter: You know, I grew up in the Northeast playing hockey and I was on the third line of our high school hockey team, which if anybody knows about lines, that's not the line you want to be on. That's one step from not being on the team. And, and I would remember going to my coach and saying, hey coach, you know, um, yeah, I'm working really hard. I'm, you know, kind of putting the time in, how can I get become a starter, How can I get from the second line of the first line? And he said, you're not that good on the third line, dude, like you're you're playing center on the third line, you're not scoring a lot of goals, which is why you're on the third line, right?

Ryan Rutan: It's that simple, right? Be better than at least one person on the second line. It's a very simple answer to that

Wil Schroter: question. And, and so, so it's it's it's not okay for him to say, you know what, I'm just gonna put you, I'm going to make you a starter, I'm going to put you on the first line because you asked for it, right? I've got to earn it. I've got to be better than everybody else on the third line and then ask for a spot on the second line and I've got to prove that I belong there right? Obviously asking for it doesn't entitle me to and I don't think anybody would think that, but conversely, the kind of sticking with that, if I asked for that responsibility and my manager, my coach in this case doesn't at least give me a path to get there, then the failings on them, Right? And and, and, and I think as a Ceo, as a founder, someone, a manager in the organization, if you don't create a path for your team to be able to step way above their level, then then that's a failing on you, right? And I think that's a huge missing an organization and I think I see it all the time, like all of corporate America for that matter.

Ryan Rutan: Yeah, I mean they talk about these, you know, the career paths and they may be well structured in terms of laying out, you know, you're an analyst level one, you're an analyst level two, you're an analyst level three. But all that's really saying is that we've created some some sort of pass fail logic gates to arbitrarily slow you down in a lot of cases because if somebody is really good then having to put in the time to prove out analysts one analyst to analyst three or whatever arbitrary bullshit roles you've made up for. People can really slow progress and that's a huge challenge within a startup company. We need everybody performing at the highest level that they're capable of. And so I think this this does create this dichotomy of saying like look, we need you to be capable of whatever you're doing, but we also need you to be stretching yourself as often and as far as you can such that we can get you to your highest level of operation as quickly as possible. There's no no incentive in a startup company. There may be incentives. I've never really thought about this. I mean there's certainly incentives incentives for the people who are already managing these folks because quite often you're talking about somebody taking over your job right or getting enough people to take over your current job or level to propel you to the next doesn't really work that way in the startup environment. And so we don't have the same incentives. The incentives are, we need to gain as much forward momentum as possible. We need to be pulling this thing as quickly as we can and and and as as hard as we can, but we can't do that without putting everybody into a position where they have that opportunity to run but are also currently doing the best they can in their job.

Wil Schroter: Yeah, I agree. And look just to be clear, I don't think everybody in the organization, you know, has to have this this Rudy moment where you know, where they're put into, where they're putting into their, this, this new responsibility. They wouldn't have otherwise had. Some people are just really good at the job that they have, right? And I think it's important to recognize that too. I don't think we've ever put a person in a position where they should have just been doing the job they had, they should have been on the third line like that. They're just really good at being on the third string and we gave them an opportunity, they failed and they kind of got disproportionately penalized for it. I think while because of who we are in the nature of what we do, we always want to look for kind of that diamond in the rough, right? We want to find that that that third string person who could be the starting quarterback type of thing. But, but let's, let's be real like only a small percentage of any organization is going to fit that mold. And, and so, so I'm just using that as a kind of a, a bit of a caveat to say. I also don't believe that people should be penalized for quote, just doing their job.

Ryan Rutan: Sure. Nor should they be penalized. I don't think for failing at the reach goals, right? When you, when you do give somebody the opportunity to run further, then their current role indicates they have the capability for you have to be a bit careful there about setting people up for failure, right? So we don't know if you can run this fast, but we're gonna let you try and I think that setting clear expectations around how much we want them to be able to run that fast, but about what happens if they don't. And I think that can also be a challenge to be super de motivating if you're given things to accomplish and either personally or through team dynamics or something else undercuts your ability to do that even if it is you, especially if it's here probably can, can be really demotivated. So I think we have to be careful in how we assign this freedom because as you said, we can give somebody enough room to run off a cliff and and that has its own dangers.

Wil Schroter: Well, I think what's interesting too is if you give someone the opportunity to kind of step up and they get to see what the next level is like and they fail. The one advantage it does give you is it gives them the understanding firsthand that they ain't ready, right? I'll go back to my hockey example because this happened right,

Ryan Rutan: coach did put me in at a

Wil Schroter: starter position, I'll never forget this. We were playing and I was a freshman in high school, we were playing puck goes into the, into the corner of the boards, I go to get it in this defenseman from the other team comes full sprint, I didn't even see him coming. All I remember is someone saying look out and then just being on my back literally seeing stars, I got knocked out, I got hit so hard that I got knocked out, right, I'm thinking to myself, no, I'm not ready for this, not ready at all. And, and, and

Ryan Rutan: I think it would have been much more fun to watch from the sidelines.

Wil Schroter: Exactly. I was like, I'll just, I'll just drag myself back to the boards right now. Um, but but my, my point is I do think there is some valuable lessons to be learned even in the, the failure, so to speak of the task because it makes you realize kind of where you are and where you're not kind of where you need to get better. I never became a better skater until I got knocked out into the boards, right? And I think, I think there's something to be said for, for um being able to see what the other side looks like. It's actually how a lot of people feel when they finally become parents and they're like holy sh it, this is hard, right way. Unfortunately you can't,

Ryan Rutan: you can't get substituted out of that game at least not easily, that's, that would be the one, the one Delta there, but you know, this is something we talked about all the time in startups, right, and it's it's fail fast, which is to say that like get to that point of failure. Talk about why we failed think about how we can do it differently next time or if we still want to do that. And sometimes, you know, in terms of the trajectory of startup, we decide that failure is for a fundamental reason and it happened and that's actually right. We don't want to do that anymore. Let's let's find a way around it. I think the same thing is definitely true within people's career progression.

Wil Schroter: Yeah, I agree. I agree. And so so with that said, you know, right, if we kind of take a look at at all of this, I think maybe some of the the, the key takeaways that I'm saying, I'd love to hear yours. One for me has always been me personally as a founder and in my case is young, Ceo not assuming that just because I was young that I didn't have the capabilities of taking on that role. It turned out that from a raw capability standpoint, I had some really good capabilities internally, I was creative, I was outgoing. I was ambitious even though I had nowhere near the experience, you know, was coming, I was a college dropout that was a theater major. Right? So I had no experience, but I could make it up in capability. I think that's that's one piece. But then the only other point I would make in all of this is that I made the mistake for a long time of projecting my insecurity of what I didn't think I could do onto the career paths of the people around me. And that was a giant mistake because at the time I really probably held back a lot of really good eggs that really just needed someone like me to let them run.

Ryan Rutan: I think, I think that is the key takeaway here and and we've what we have and we'll talk about this again, but it's about using the wrong measuring stick to measure something, whether that's the success of your startup, the capability of an individual, the value of their experience in the past, their potential as somebody moving forward. I think that when we try to draw too many lines from too few and very disparate and sometimes very murky data points, we've really run the risk of getting the wrong answer when the right answer is to try and see right to let things prove it out to set up test environments that will allow us to come to the actual conclusion, because in most cases, both in terms of, you know, starting a company and being a member of that company, whether you're leading it or just contributing to the success of the company, the proof is in the pudding agreement, there's no real way there's no crystal ball that's been developed to let us see that future. And so I think that it's it's important to put ourselves in positions where we're able to truly see that in reality. And not to let our preconceived notions or guesswork get in the way of real success agree well that's going to do it for this episode of the startup therapy podcast. But in the meantime, if you love what we're doing, head over to itunes and subscribe and comment. If you want to contact us directly. We're not hard to reach email us at therapy at startups dot com will and I respond to every email that comes in. Please don't be shy what we learned today is a tiny fraction of the help that you can get from startups dot com. Whether you need to learn how a startup gets built to find a mentor or raise capital to find new customers or if you just need to connect with founders who are dealing with the same ship you are, you'll find it on startups dot com with all that said, let's get back to building our startups. This is Ryan Rutan for my partner Wil Schroder and the entire startups dot com community saying goodbye for now. Friends

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