YouSaid · the spoken record

Jason James

lines on the record: 56
first: 2025-08-29
most recent: 2025-08-29
sittings or episodes: 1
sources: podcast

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“The thing that I know now that I wish I knew then, the hardest part won't be building the technology that can be like an end-to-end autonomous AI recruiter. The hardest part is going to be change management. Working with the humans to adapt and get comfortable with a total paradigm shift. In hindsight, it's obvious, but we were more fixated on figuring out, can it do it than what it would take to get people comfortable with the emerging technology change and how dramatically it'll affect their working lives?”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, it's a good distinction. We try to build relationships between rounds and with people that have potential to be high quality partners. That's effectively what you're bringing on is capital and a partner on your journey. And so it's worth building the relationship and getting to know folks outside of the funding cycle. But then once you're in it, you're in it. By getting to a tight process, it's really like getting to a moment where someone's at least like verbally expressed and committed that they're interested. They're going to go deep on diligence and stuff like that. Then, okay, we'll be flexible. We'll figure out like how to close out the next, you know, a couple weeks and not be a pain in the ass because we want to be good partners and collaborative about it. But otherwise, you can just get strung along and not really know where you stand because it's in their interest to like just kind of keep you in the mix.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“What I didn't understand about fundraising when we first set out is the game that we're playing is as a company, we're looking for a yes. As an investor, it's in their interest to preserve optionality for as long as possible. Super easy to get meetings. Meetings mean nothing. And I thought, holy shit, we have all of this interest. This means that like it'll turn into funding any day now. No, it doesn't actually get real till you get like that first term sheet in and then all of it clicks everything turns a corner and it's very important to time box it's very important to sort of drive towards that first like term sheet in and then run of quick process after that first term sheet is in but everything else is i guess kind of theatrical um until that point”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“I think that the threshold of Call it Series B, it's probably not a great return on the time for CEO or like a founder to be in every recruiting loop. They are still the pace setter, the bar setter for the company in terms of talent density and talent philosophy, but they should set some threshold for themselves of like senior manager and up or something like that. Because what you don't want is C players hiring other C players. And so I would, at a certain point, transition from interviewing ICs to like interviewing only management or something like that.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“And so, okay, they'll take the call. Maybe they know someone and it's network based. But they can't find out of a thousand potential rules, what's the exact two or three that are like going to be what they want? That is incredibly hard. I think that we move from casting a wide net on the employer side and casting a wide net on the candidate side to more of that like dating matchmaking model.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“I think for the future of hiring, we're at is, at least within investors, there's consensus as to AI agents will do much of the hiring work. That hasn't proven to be true yet, but is now sort of coming to be like a consensus point of view that it's an inevitability. I think the next big wave that we haven't internalized or worked through is just how much inefficiency there is to the process of a candidate finding a company, the future is going to, when it comes to recruiting, it looks a lot more like dating where it's like there's two swipe rights equal a match, then it's like a double opt-in, like warm intro versus most of today how a candidate finds a company is wildly random from job boards to they happen to get a ping from a”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, 100%. I'd given up on dictation for a long time. I just didn't think it was worth it because editing was slow and clunky. But whatever they're doing, they nailed it.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“Best recent purchase under $500 was a subscription to Whisperflow. I spent so much time writing and communicating. It's amazing. Now I have largely like stopped typing and it's really good. Like it actually works. And I also don't have to edit. I can just ship it. And it's returning a lot of time for me.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“At linear, I'm going to just assume CEOs are product leaders. He's built that company on his own terms and the quality of linear is incredible.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“So, yes, DoorDash did beat Instacart. I mean, why did that happen? I think the main thing is they expanded faster, went, you know, beyond restaurant sooner. I think also their key insight was when the suburbs, they got there first, beat Uber Eats to do that. And so they won a really, really big way, which then gave them room to be able to expand into other verticals. Whereas Instacart should have gotten into restaurant year five, year six, and should have also gone international way sooner.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“Yes. Yeah, founder transitions really hard. I think Fiji did it really effectively. She's got a lot of like charisma and charm. And so she endeared herself to the company pretty quickly. That made the transition smoother. The fact that she was on the board also, like there was some continuity of context and stuff like that. And Aporphus participation in finding and recruiting her led her to be someone of a similar pace. There was some continuity, but still like you lose a lot when the founder CEO moves on.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“I think a little bit goes a long way. We spend the first five or ten minutes praising people for like awesome shit that they did. And I think some investment like that along the way is useful because you don't know when ripping growth becomes slow growth, becomes no growth. And having some goodwill in the bank from people that like each other and that retains them is useful”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“Thumbtack, amazing culture, incredible workplace. I would love to have worked there forever. And Instacart, incredible business, but neglected culture, not a pleasant place to work.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“Lower the culture amp surveys get worse in terms of their score. And so I've at times, and I've seen other CEOs at times, like fall down the trap of caring and trying to optimize the culture scores and stuff like that. But it ends up, it never satisfies. So what I saw from like Apurva, like with Instacart, just a relentless focus on growth. And it works out until growth slows.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“The thing that I've learned is culture really starts mattering and you start talking about it a lot when growth slows. And what I found is like the only thing that matters for culture is growth, like business growth. Because for a business that's growing at like an amazing clip, it's always going to have cultural sort of issues that make it kind of suck to like work there. But everybody's okay with that and leaned in because they see a path for themselves. Because what they're solving for will be more comp, more career progression, bigger scope, manage a team. And they have a line of sight towards that. But then if you don't have enough growth, then everybody starts worrying about their seat, their path, and it gets political. It gets slow.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“Oh, like, why would a company glorify 99 It's incredible marketing. It's a way of differentiating against sort of the market. Everybody's going to be intent, but we're super intense. And so like we're going to be like Olympians and in terms of work ethic. It's like a coded way of saying, hey, we're self-selecting to like 20 to 26 year olds. So you'll end up with a lot of like junior and mid-level people that are working very hard, but also socializing very hard tends to be true in these types of cultures. And at the end of the day, like 72 hours a week actually isn't that much, like for me at least where like I've metabolized that over time to be like a normal week. But it does help with their sort of recruiter brand, their employer brands to be like, we're for the really intense people that”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“I haven't found that work cultures have changed in my observation based on AI in terms of their intensity. I think of Instacart as effectively pre-AI and super intense. A good week was 60, 70 hours, a bad week is 100 to 110. And maybe this is just at like VP level or something like that. At 11 p.m., 12 p.m., I could ping anyone on Slack and they were already online and they're immediately responsive. And so it was like an around the clock culture. And I think we're still pretty intense at Daisy. We're not. We're not that extreme, but maybe what's changed is I feel like the glorification of like 996 by certain companies has been”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“We've solved it both at Instacart and TZ with basically required versus optional attendees. So project team opts in. They invite themselves required for us right now is me and my co-founder. And then the rest of our R&D team is optional. They will opt in if they have availability or interest in the topic. And so we usually end up with eight or nine people. The way I worked at Instacart was product reviews for the consumer app was me, my engine counterpart, my design counterpart, my data science counterpart, and then my senior directors across the various pillars of the product and then the project team. And so they always have a good quorum to provide feedback, but doesn't necessitate everyone. One all the time, you know, being in every meeting.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so for Taisy, and then eventually at Instacart when I worked through this, we just have recurring time slots that are always available to book every single week. So we have six time slots for reviews. Anybody can grab one at any time. And it's to get more eyes and feedback on a particular thing that they need feedback on. It could be really early in the life cycle. It could be like right before they ship it. It could be design. It could be engine, it could be just a requirement. But anybody can grab the time when they need it with that. Since they're selecting into it, it's at the right time for them. And they have a particular question. When it goes the other way around, they show up and it's more about optics and managing upward when I'm saying, hey, bring this project on this date. I want an update.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“I've learned a lot about product reviews through trial and error and how they sort of have worked across many different companies. One of the most important things I found is it needs to be like self-serve and like opt-in when myself or, you know, my bosses try to make it pull, not push. What it does is it changes the like life cycle of the project to where now it's anchored around like getting things ready by a certain date for an internal milestone for an internal review with leadership versus if we let it be self-serve and more push than pull, then if constructed right, if coached right, they will bring it at the right times and it will be a help, not a hindrance.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, at Thumtack, you know, conventional wisdom is remove friction from onboarding, make it easier, faster, whatever. What we found was that doesn't actually work for our product where the friction was answering questions about your project that you're trying to accomplish. When we take away certain questions at a certain point, like the results that we deliver as far as pros that are a match for your project deteriorates. And so like friction of capturing those questions and the drop off that sometimes occurs is useful because it'll get people to a point of success. And that success is worth more than the drop off that we incurred.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“I think the timing for value abstraction ideally is always based on what would maximize lifetime value. So if you have a reasonable hypothesis that by delaying value extraction, you can achieve a greater sort of lifetime value extraction over the long term, then delay it as long as you can survive as a business in the interim. Yeah, if you don't have that hypothesis and you're just hoping it becomes valuable sometime, it's not a business to sell a dollar for a dime. And so don't do that.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“I think that that could be a CPO's job in a certain company. Like, what do I imagine the It's the thing why I get into product, at least, and what I value is the creative, like aspect of it. It's building something new, process management is a means to that end. And I want to spend as little time on it as is necessary to achieve the end, which is shipping great product.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“It's not hand wavy. It's not platitudes. It is like a clear, a crisp articulation of what we should do, why we should do it. And at the end of that process, we will have either validated or invalidated. But what I find is when a CPO can make a whole career out of being hand-wavy, it's like kind of like a magician where there's like a misdirection and sleight of hand to say like, hey, we're going to do this and we're going to do that. And like when you don't put numbers to it, when you don't put dates to it, there's just like a complete lack of accountability or the accountability moves down. And it's always a director's fault or, you know, some VP's fault. And so those types of things like obscure what really is the CPOs to own.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“The only thing that matters with the CPO is whether they have the trust of the CEO. And so if they have the trust of the CEO, then they can stick around and they'll likely sort of be successful. And if they don't, they're going to continually buttheads and it's just not going to work out and the role will turn over every year and a half, two years. In those situations, the CEO should just do the job because they need to learn through doing. And in doing the job, in thinking harder about the problem, they are the only ones that really have a shot, I think, at cracking it. And I guess how does the CPO establish trust? I think it comes from results. So they say a thing. They were right. It delivered the results. And so being consistently right a lot builds trust and clarity.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“Assume, like most founders are product people. I think that that tends to be true. I honestly think you don't need a CPO until maybe like as a founder you're starting to think about transitioning into the chairman role.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“Here's the product. I have a crisp product vision for where we're headed. I have a crisp workplace vision for like who we are and what our culture is. I have a crisp vision for growth. That, I believe, belongs with the founder. And until they arrive at a place of like clarity for themselves, they're not going to get it through somebody else.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I've seen this movie many companies over the last 15 years. The three roles that I see that get fired over and over are CPO, CMO, and head of talent. They typically have like one and a half to two-year stints, and then they move on to their next thing, you know, sort of like quietly and discreetly. So most folks don't understand that they were fired. But when you're in the senior leadership team, you do. Why does that happen? I think it's very similar to the same deal of like any mishire. It's muddy thinking. And it's like founders vaguely know what they want. They want the product to work. They want the business to grow. They want to make good hires. But the level of clarity and vision of like, okay.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“But you just don't have to have them full time, which also then creates more flexibility about how we manage cost and burn and stuff like that.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“Put a real premium on getting to the right answer quickly, and it's hard to find those people. But when you find them, that they can take in the context, they understand the problem, and they're going to solve it in a way that is simple, clear, and quick. I will hang on to those folks for like the rest of my career. And I have. I don't know how to always get there. Like, I don't know it on the front end. I only know it through like doing. But I do like working with part-timers or fractional people because I get to try it before I buy it. And then sometimes it's like, oh, this really, really works. And so we found that like three or four times already in the last year with some part timers. So I would advise founders try it a lot. If you can get the people to do some work like embedded team members.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“Change of pace. It's hard to find a way to contribute when you don't want to sign on full time to do a 15, 20 hour a week like PM job. And it's been remarkable, actually. So I've worked with like 100 PMs probably over the course of my career. I like his 15 to 20 hours more than most of their like 50 to 60 hours.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“As a founder, I find that everyone wants to give me advice and get paid for it. And for the most part, I don't need it. There's a few key areas where advice has been useful as it pertains to fundraising or go-to-market because that's like hasn't been a strength or part of my background or my co-founder's background. But by and large, I find advice to be like cheap. I can get it for free if I want. So I don't know why I would pay for. What is useful is people that'll put in the work. And so this guy, Colin, as that advising companies since leaving Slack, I got connected to him through my wife, who was an engineer at Slack and worked with him. And my pitch to him was, hey, wouldn't you like to get in the game a little bit? And instead of just, you know, give advice, like, can we do some work together? And it's a nice.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“If I think about the founders and experience sort of veteran like myself and my co founder, we're like, we're 40 plus, we've been in the industry for one or two decades. Yeah, like we can pull those folks. But when I think about, okay, new grad or like dropout, I don't think they actually need it. I think you just need people that are going to be like very competent and very driven and very ambitious and hardworking and stuff like that. And that'll get you plenty far to where you've earned the right, I guess, to be able to get some remarkable people to come work for you. But I don't think it's essential to get off the ground.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“This outcome. And you'll hopefully get some real talk based on that. If they did big things, that's incredible. Then they have great resume and they contributed, but sometimes you can't find it.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“I've learned a lot about interviewing from Apurva, founder, CEO of Instacart. He spent like seven hours with me over the course of maybe four weeks when recruiting for the VP of design role he was trying to fill. And much of it was just my questions for him. Like I probably had 100 questions for him. His like one question for me was like maybe I had three questions, but like the one that stuck with me was just like what did you do? And like I'd say some things like, no, but like, what did you really do? The more that you kind of like keep pushing at that question, what you'll hear is either like platitudes or like depth and specificity. And then you can take that and triangulate it, like back channel with like other folks and like their orbit. Hey, so how instrumental was this person to?”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah. And I've gotten this wrong, so I get sort of why it happens. But a lot of people hire for a resume. And I found some of the worst hires that I've made, some of the worst hires I've witnessed are based on incredible resumes. And I think why people get that wrong is you mistake that this person was in a seat at a certain time. And in many ways, it was an elevator going up and they were on the elevator. But what we failed to understand was like, what did they do? Like what did they actually do to like change the trajectory? Did they contribute or just were they at the right place at the right time? And I find that right place, right time can get you really far in terms of getting big roles and stuff like that. But you get found out after like a year, year and a half. And so.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“Ton of people. And I also look for help from other people that have hired for the role. And so, hey, who do you know? Who's good at this? And at least I can talk to that person, even if they're not on the market about what I should be looking for.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“Me, at least, how I figure it out is I start from the outcomes that I'm trying to achieve. So what would actual success be for this person if they did the job for 30, 60, 90 days? Like, how would I actually be happy with them? What's true about our culture that they just need to have a level of grit, drive, ownership, that sort of thing. And so I try to articulate that and make chat GPT or Max Daisy agent output it as a JD, post it. And I just really need to start talking to people. For me, I learned through talking to the first 20, 30 candidates to get a feel for at least some pattern matching across them of what is an excellent answer sound like versus not so good. But initially, I can't tell the difference. So I have to just talk to it.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“I think the most common way that I see hiring managers screw up hiring is like over delegation, which then is compounded by the fact that they have muddy thinking. They don't know what they want and they haven't taken the time to really suss that out. So then you think you're hiring a recruiter and it's the recruiter's job to hire for you. But the recruiter doesn't really get what you want because you don't know what you want. And so I think the best hires will come from like super active involvement by the hiring manager that they are in it and very hands-on. But most hiring managers think that they've outsourced it and they are hands off and it doesn't go well.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“For us, it's about the thesis that we're trying to test. And in order to be able to validate or invalidate the hypothesis that we have, it requires certain things to be true. If we'd only built like an AI sourcing tool, let's say, where you can create a list and email candidates and stuff like that, like much of the market is today, that would lead us to be selling to recruiters and it would then be about efficiency of the human recruiting team with an AI enabled tool. That wasn't thesis that we were trying to test. What we're trying to test is, can AI be a labor capacity addition or augmentation for a company? And so that needs to be like the breadth of a human sort of role. And so for us, that necessitated building more.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“Companies are tired of point solutions and they don't want to integrate another one. What we've struggled with is it's a lot of surface area and it's hard to get 12 things to a sufficient quality level. The thing that I learned from it is you can't do an MVP for a breath first approach. And I think Ben, the CEO at equals, has a post on this where it's basically MVP versus full build. And so they have a spreadsheet. We took an MVP approach to a full build breath product when really we should have delayed going to market by another six months to get it all to like a higher quality level.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“Think the biggest non consensus product decision that I made that didn't work is how we built DACY, like the V1. We took a breath first approach, the consensus view is, you know, start narrow, point solution, land and expand. It's the wedge, that sort of thing. What we set out to build is the equivalent of a full life cycle recruiter. And so that necessitated a ton of surface area across the entire recruiting journey from opening an offer all the way up or opening a role all the way up to the point where you're ready to extend an offer. That was the product scope. So very broad. What was right about that is it's a very differentiated positioning and has helped us get a ton of meetings and customer interest because”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah. I hate consensus building. I think it leads to slow execution and often worse outcomes that it lacks anyone's conviction because it ends up being watered down that like this is the right thing. So I'd rather have someone feel empowered to make the call test learn and like either be right or wrong, but like get to an answer quickly so that they can move on to the next thing.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“More usage, whether they desktop and mobile, is better. So, yeah, let's just go all in and we'll see what happens. So I guess it helped me see the value of even in late stage companies of conviction-based bets that are based on like sensible, secular long-term trends or otherwise.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“Me, the biggest product lesson from Thumbtack is you should just do the common sense things. And whether you have the data to support them or not. And chasing the data to support why we should do something can actually just be a distraction and a delay. And so to unpack that, what I mean is I recall so much time we spent hemming and hong in 2016 through 2018 about whether we'd be native first, like how important app usage was versus web usage. And we knew it was correlated to retention, but we didn't know if it was causal to retention. And to do sort of analysis and study to determine the causality of something takes quite a long time. When at the end of the day, we could have just said, listen, the long-term secular trend is everything's moving towards mobile.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“Think where PMs spend their time will evolve. And by that, I mean instead of long PRDs and like a set of requirements or like even just the idea of like CEO of the product, I think is really obnoxious and not helpful. So a good PM will be filling gaps that a team has. And I think that there will be continual gaps. It is hard when you're in it. in the thick of building things to be able to zoom out and say, okay, of the 50 things we might do, what are the like three that we should do, like next cycle? And how do we prioritize against the customers we have versus the customers we want versus fixing what we've already built versus new capabilities? That requires a building a lot of context. Think that that continues to be where PMs spend a lot of time, but articulating it in some doc, it becomes a one-pager instead of a 20-pager.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“I see PM as think of it as like a hire of last resort. And so I don't think a company should be allergic to hiring them, but it shouldn't be the default. And why is that? Creating room for engineers and designers to be leaned in on the business is good for the business and that having more ownership versus, hey, stay in your lane, design the thing, hey, stay in your lane, code the thing leads to deeper employee engagement, helping them think like a founder about all aspects of the business. But if not having PMs is affecting execution, the team is asking for PMs, then that's, I think, the time to introduce one.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“Call it 50 people or so. We actually do have some gaps. And so we have PM that's like former senior director at Slack that contributes about 15 hours a week. And it really helps fill the gaps on his enterprise experience, clarifying the requirements, prioritizing. Because as good as our engineers are and as good as our designers are, it's just helpful support to them.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“And some designers could have always done it. And so that's how I transition from design into product management is it's not really different. Like design is a set of decisions about a product. And so those decisions can be made by an engineer. They can be made by a designer. They can be made by a product manager. So I don't see the roles as all that distinct. It's just sometimes you're lacking skills within the team. So then you need somebody to bring those skills with emerging technologies. Perhaps you can have more skills, basically. So an engineer can get to something like solid design wise when it might have been challenging for them in the past. That's great. And same with a designer could perhaps be able to code up something through prompting. And that's amazing. Like for us, my theory was we didn't need PMs until”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source
“So, the way I see roles evolving is really towards what I think has been more natural and organic all along. When I think about early days of tech, it's like engineers. And then they were building and all of a sudden like UX actually mattered because we had like graphical user interfaces and some of them could design and some of them couldn't design, you know, they couldn't imagine it and like make it usable. And so design as a field, UX design as a field emerged. Then what happens is product emerges because someone needs to understand the business requirements, why we're doing what we're doing.”
2025-08-29 · The Twenty Minute VC · 20Product: Why Most CPOs are Bad | Why You Do Not Need PMs in a World of AI | Why the Design Stage is Dead and How to Use Vibe Coding to Replace It | The Three Roles All Founders End Up Firing on Repeat with Jason James @ Tezi · IDENTIFIED FROM THE TRANSCRIPT · source