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

Jason James is the Co-Founder of Tezi and one of the leading product minds in the valley. Prior to Tezi, Jason was the VP Product at Instacart and before that was Head of Product and Design at Thumbtack. AGENDA: 00:00 Product lessons scaling Instacart to $40B – what really moves the needle 02:15 Why “quick optimizations” won’t build billion-dollar products 04:30 MVPs are dead? How AI is reshaping product development 07:00 Do startups even need PMs anymore in the age of AI? 11:30 The biggest product mistake Jason made building Tezi 16:30 Why most hiring managers fail at recruiting 20:00 The resume trap: how to spot if someone was just “on the elevator up” 26:00 The three roles founders always end up firing 28:00 Are most CPOs actually terrible? 36:30 The myth of startup “culture” – why growth is the only thing that matters 43:00 Did DoorDash actually beat Instacart? The inside take 48:00 Fundraising secrets founders never realize until it’s too late

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Harry Stebbings?

  You are listening to 20 Product with me, Harry Stebbings. Now, 20 Product is a show where we dive into the best product minds in Silicon Valley to unveil how they think about building product teams, managing PMs in a world of AI, how they build the best products and product teams today. Now, we're joined today by one of the best, Jason James, co-founder of Tezi and one of the leading product minds in the valley. Prior to Tezi, Jason was the VP of Product at Instacart, leading up to their IPO. And before that, he was the Head of Product and Design at Thumbtack. But before we dive into the show today, are you struggling to beat model benchmarks or implement Gen AI in your product?

• 0:37Harry Stebbings?

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• 1:20Harry Stebbings?

  and then finally, learn how Turing can refine and implement your models for better performance. Take the guesswork out of Gen AI. Visit turing.com/20vc to start your free assessment today. And once your Gen AI strategy is on point with Turing, You have now arrived at your destination. Jason, I am so excited for this dude. I've been looking forward to this one all day. So thank you so much for joining me first.

• 1:45Speaker 01

  Yeah, really happy to be here. Thanks for having me.

• 1:48Harry Stebbings?

  Now, I want to start a little bit before Tezzi, and I want to start with, you've been at some of the most incredible organizations from your Instacarts to your Thumbtacks. If we start breaking them apart, actually, with Instacart, when we think about big lessons learned, what was your biggest product lesson learned from the days at Instacart?

• 2:08Speaker 01

  Biggest product lesson learned from Instacart was as much as A/B testing and like high velocity optimizations feel like progress and to some extent, they will be. When you're at a business of that scale, where we're talking like 30 to 40 billion in gross transaction volume, the only thing that really moves the needle is like new capabilities. So we would try and test a lot throughout the customer experience to optimize conversion, make things easier, make search better, the results more relevant. And it would deliver wins, but the sleeper huge win was when we launched Snap EBT,

• 2:53Speaker 01

  which is like food stamps, to be able to pay with those on Instacart. It became a billion dollar business line in less than a year and then grew up to be four billion. So it changed how we plan and how we think about placing bets from what are the quick win optimizations on the current experience to what do we need to do to unlock the next billion to five billion?

• 3:20Harry Stebbings?

  So if you're an early stage founder then, listening to this and building as you are today, how does that change your advice as to how you would advise a founder to allocate team and resources between optimizations and iterations and new capabilities and kind of game changers?

• 3:37Speaker 01

  So how I translated that into Tazie, where we are seed stage, is if we can launch a new capability and do it at like an A quality level, we can actually set it down for a while and not have to come back and keep working on it for, call it a year, which then enables us to be able to go and add an additional capability. But when we launch things that are like MVPs, that are just kind of like scrappy, like beta stuff, we get mired in fixing it and trying to make it work. And it slows down our ability to launch sort of the next big thing that's going to move

• 4:20Speaker 01

  the needle on our ability to have a differentiated positioning and to like market ourselves.

• 4:26Harry Stebbings?

  Does that mean that you don't agree with the kind of test it, ship it, quick and dirty, get customer feedback and sticky tape from there?

• 4:35Speaker 01

  Sort of. So I guess, how do I feel about like MVPs and test and learn? It's when we're building, we'll have varying degrees of clarity as to what the customer needs and wants, based on everything else that we've learned from customers over the last, you know, year, year and a half at Tazie. And when we have clarity as to what they want, let's just build the thing. Now, where there's ambiguity and we're unsure as to, does this really meet their needs? There's so many steps along the product development journey that we can bring in a customer. And like whether that's at the design stage, whether that's with a prototype alpha that was vibe coded, to right before launch, we released to just a few customers.

• 5:20Speaker 01

  And so I think of it as kind of like one swing and I want to finish the swing. But in between, we will need to involve customers if we lack certainty.

• 5:32Harry Stebbings?

  Can I ask you, in terms of that MVP stage, how has that changed in the world of AI? You mentioned vibe coding there. Do we skip the design phase entirely and just move to a vibe coding prototyping stage? How's it changed with AI?

• 5:45Speaker 01

  It's really changed it dramatically, even just in like the last year for how we work. Our designers now are trying to figure out what vibe designing means. Then to some extent, even if they can vibe code, there's some ways in which it works. And so magic patterns has been like useful for us to designer can just articulate what they want, what they're trying to do. And then all of us can see a prototype and interact with it and get what the designer's trying to put forward very quickly, very simply. We haven't quite gotten to the place where the designer can use cursor to like vibe code it themselves. We've tried, just running an environment was too hard.

• 6:25Speaker 01

  And so maybe someday we can optimize it so that, you know, a designer or myself could stand up an environment and do it pretty quickly. But it's enough that, okay, this vibe designed thing in magic patterns works for the engineer to vibe code it up themselves. And sometimes it'll be high quality code and sometimes it's going to require, you know, a bunch of work after that. Our standard for what we release is still the same. Like we still want to get to like A quality on anything new, but we can get there faster.

• 6:57Harry Stebbings?

  Can I ask, do you think you see then the continued segmentation of roles between design, as you said there, who maybe use magic patterns, but still a segmented role, and then end who still a segmented role, but use cursor to be more efficient? Do you think we have the same, or do we see the bundling where all of them come into one product engine design and we have this kind of uni superhuman being?

• 7:19Speaker 01

  So the way I see roles evolving is really towards what I think has been like 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 like couldn't design, you know, they couldn't imagine it and like make it usable. And so a 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 and articulate and prioritize that. But the thing is, some engineers could

• 8:04Speaker 01

  have always done it 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

• 8:48Speaker 01

  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, 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 fifteen 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.

• 9:24Harry Stebbings?

  Do you think early-stage companies do need PMs? It's always been hailed that, you know, get the PM in, they're the CEO of the product. But now we're seeing this kind of swing away from PMs. How do you feel about advising an early-stage founder on whether they do or don't need a PM?

• 9:38Speaker 01

  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.

• 10:22Harry Stebbings?

  Does the role of a PM change in a new world of AI where vibe coding is so prominent? Where speed of development is so changed? Does the PM role change and does the skills required to be a good PM change?

• 10:35Speaker 01

  I 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 fifty things we might do, what are the like three that we should do? Like next cycle? And how do we?

• 11:16Speaker 01

  We prioritize against the customers we have versus the customers we want versus fixing what we have already built versus new capabilities. That requires a building a lot of context, and I think that that continues to be where PMs spend a lot of time. But articulating it in some doc, like it becomes a one pager instead of a 20 pager.

• 11:41Harry Stebbings?

  Can I ask you if we said there about kind of Instacart and the importance of building new capabilities over iterations and optimizations? If we discuss Thumbtack, another incredible company, when we think about lessons learned there, what was the biggest product lesson from Thumbtack?

• 11:58Speaker 01

  For 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 hawing 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.

• 12:40Speaker 01

  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. 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 like late-stage companies, of conviction-based bests that are based on like sensible, secular, long-term trends or otherwise.

• 13:18Harry Stebbings?

  Do you think you should have a decision-making structure where people are able to make decisions fast versus seek consensus and debate?

• 13:28Speaker 01

  Oh, yeah. I hate consensus building. I think it leads to slow execution and often like 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.

• 13:57Harry Stebbings?

  What's the biggest non-consensus product decision you made that didn't work? And what did you learn from it?

• 14:03Speaker 01

  I think the biggest non-consensus product decision that I made that didn't work is how we built Casey, like the V1. We took a breadth-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 lifecycle recruiter. And so that necessitated a ton of surface area across the entire recruiting journey from opening an offer all the way up and or opening a role all the way up to the point where you're ready to extend

• 14:43Speaker 01

  an offer. That was the like 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 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, you know, 12 things to a sufficient quality level. The thing that I learned from it is you can't do an MVP for a breadth-first approach. And I think Ben, the CEO at Equals,

• 15:24Speaker 01

  has a post on this where it's basically MVP versus full build. And so they have a spreadsheet product and you had to take like a full build approach. We took an MVP approach to a full build breadth product when really we should have delayed going to market by another six months to get it all to like a higher quality level.

• 15:48Harry Stebbings?

  How do you know whether something's full build or MVP-able? What's that difference between the two?

• 15:54Speaker 01

  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 the thesis that we were trying to test.

• 16:35Speaker 01

  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 like building more.

• 16:54Harry Stebbings?

  I always think about the road to the start line and what is required to get feature parity in a product? And how difficult is that? We often see it with like messaging products, where actually messaging products is quite difficult to even just get to parity with any of the leading messaging providers. And then you're only equal. And that's not that compelling. You mentioned there like, hey, if we'd only focused on sourcing or only focus on an initial core segment or wedge. When we spoke before, you said something that I really liked. You said most hiring managers hire poorly. And I totally agree, dude. I've interviewed, you know, a thousand of the best founders of the last decade, literally. And 50% is the strike rate on like good hiring.

• 17:36Harry Stebbings?

  Okay, so what are the most common ways that people screw it up?

• 17:41Speaker 01

  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 like muddy thinking. They don't know what they want and they haven't taken the time to like really suss that out. So then you think you're hiring a recruiter and it's the recruiter's job to like 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.

• 18:25Speaker 01

  But most hiring managers think that they've outsourced it and they are hands off and it doesn't go well.

• 18:31Harry Stebbings?

  Don't laugh. What's the best way to know what you want? I know that sounds super meta, but say we're hiring an engineer. What is the right way to know what we want? Should we write out all the daily tasks? Should we write out the values, the skills? How do I know?

• 18:46Speaker 01

  For me at least, how I figure it out is I start from the outcomes that I'm trying to achieve. So what would actual like success be for this person? If they did the job for thirty, sixty, ninety days, like how would I actually be happy with them? What's true about our culture? That they just need to have like a level of grit, drive, ownership, that sort of thing. And so I try to articulate that and make chat GPT or, you know, our 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 twenty, thirty candidates to get a feel for

• 19:30Speaker 01

  at least some pattern matching across them of what does an excellent answer sound like versus, you know, not so good. But initially I can't tell the difference. So I have to just talk to a 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.

• 19:57Harry Stebbings?

  So they don't know what they want is number one. Any other ways where people seriously make mistakes on hiring in that core first process?

• 20:06Speaker 01

  Yeah, and I've gotten this wrong, so I get sort of why it happens. But a lot of people hire for resume and I've 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?

• 20:48Speaker 01

  And I find that right place, right time can get you really far in terms of getting, you know, big roles and stuff like that. But you get found out after like a year, year and a half. And so those are, you know, often execs that turn over quickly and it's unfortunate.

• 21:06Harry Stebbings?

  I'm an early stage founder and you're my friend helping me. There's a person with a stellar resume who looks great. How do I determine if the stellar resume is justified and great, we should hire them versus they're on the elevator going up? What questions depict that? How do I unpack that?

• 21:23Speaker 01

  I've learned a lot about interviewing from Apurva, founder, CEO of Instacart. He spent like seven hours with me over like 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 a hundred questions for him. His like one question for me was like, he maybe had three questions, but like the, the one that stuck with me was just like, what did you do? And like, I'd say some things and then he's 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.

• 22:06Speaker 01

  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 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.

• 22:30Harry Stebbings?

  Do you think fundamentally it is so competitive today? That if you're an early stage company, you will never have a great person who has contributed with a great resume want to join your company? Like, do you have to find diamonds in the rough? Because it's so hard so early that no one who's been there and done it wants to go back.

• 22:50Speaker 01

  If I think about the founders and experience sort of veteran like myself and my co-founder, where 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 like and like 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.

• 23:29Harry Stebbings?

  You mentioned the 15 hours a week that the person from Slack partakes in with you. How do you advise founders on part-time advisors in that respect, which you see more and more of?

• 23:42Speaker 01

  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, it 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 like, 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, has been advising companies since leaving Slack. I got connected to him through my wife, who was an engineer at Slack and worked with him.

• 24:26Speaker 01

  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 change of pace. It's hard to find like a way to contribute when you don't want to sign on full time to, you know, 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.

• 25:02Harry Stebbings?

  Why? What makes it so successful in a way that founders can learn from?

• 25:07Speaker 01

  I 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. So 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.

• 25:49Speaker 01

  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, but you just don't have to have them full time, which also then creates more flexibility about, you know, how we manage cost and burn and stuff like that.

• 26:10Harry Stebbings?

  You said something brilliant before, which is about founders tend to fire the same three roles over and over. It was a bit of a cliffhanger. What are the roles that they tend to fire over and over? And can you unpack that statement for me?

• 26:25Speaker 01

  Yeah, I've seen this movie at, you know, 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 like 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 mis-hire. It's muddy thinking and it's like founders vaguely know what they want. They

• 27:10Speaker 01

  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, here's the product. I have a crisp product vision for where we're headed. I have a crisp like 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.

• 27:41Harry Stebbings?

  You mentioned CPO first there. A CPO is this kind of hailed role. If you were to advise me as a founder, when is the right time to start thinking about hiring a CPO?

• 27:52Speaker 01

  I'm going to 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.

• 28:08Harry Stebbings?

  Do you think most CPOs are shit?

• 28:10Speaker 01

  Yes. Yeah, absolutely. Yeah.

• 28:12Harry Stebbings?

  How do you know? How do you know if a CPO is shit? Like I interview a lot of CPOs. How do I know if they're shit? If they say alignment a lot, like what are the buzzwords?

• 28:23Speaker 01

  The only thing that matters with a 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 butt heads 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?

• 29:06Speaker 01

  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. 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.

• 29:47Speaker 01

  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 like really is the CPO's to own.

• 30:09Harry Stebbings?

  I often find the weak CPOs oscillate a lot around process implementation. And it makes it sound really scientific and structured in a way that they know what they're doing, but in a way just adds a level of bureaucracy. Would you agree with me in that reflection?

• 30:24Speaker 01

  I think that that could be a CPO's job in a certain company. Like, what do I imagine the CPO of like ADP does? I would imagine it's along those lines because it's a big org. It's hard to wrangle a lot of people. And so most of the job is wrangling and aligning. It's not a very fun job, but like, I'm not here to like necessarily disrespect it. I think it's probably a necessary job, you know, at that scale of company. But 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.

• 31:08Speaker 01

  And I want to spend as little time on it as is like necessary to achieve the end, which is, you know, shipping great product.

• 31:16Harry Stebbings?

  Is there ever a time when you should let beautiful design hinder value extraction or time to value extraction? In other words, the customer experience is so delightful, but it takes a bit longer to get value or it's less obvious how to get value. Is there ever a time when the priority should not be value extraction for the customer?

• 31:38Speaker 01

  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, you know, as a business in the interim. Yeah, if you don't have that hypothesis and you're just hoping it becomes valuable sometime, like it's not a business to sell, you know, a dollar for a dime. And so don't do that.

• 32:13Harry Stebbings?

  It's interesting when you say that, I think about Noom, the weight loss product, where the onboarding process is very significant. But to your point on the value extraction over the long term, the lengthy onboarding process leads to a much superior long-term product experience for the customer, where in the short term it's hindered for better long-term value extraction.

• 32:33Speaker 01

  Yeah, at Thumbtack, you know, conventional wisdom is like 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. The, 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.

• 33:16Harry Stebbings?

  Can I ask, when you think about the drop offs that incurred, reflections on product launches, how do you think about product reviews today? Any lessons on what it takes to do great product reviews?

• 33:27Speaker 01

  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

• 34:12Speaker 01

  right times and it will be a help, not a hindrance.

• 34:17Harry Stebbings?

  What do you mean push, not pull when it comes to product reviews? Just so I understand that.

• 34:21Speaker 01

  Yeah. So for Tazie and then eventually at Instacart, when I like worked through this, we just have recurring time slots that are like 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 edge, 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

• 35:05Speaker 01

  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 and I want to like make sure, you know, it's on track.

• 35:19Harry Stebbings?

  Do you not benefit from the combined engagement? And what I mean by that is by having a set weekly time, that one time where 10 people come. If you have three come on Monday and three come on Tuesday and three come on Wednesday, the lack of mind share, combined ideas is spread across three days, not one, and you don't get that benefit output. How do you think about that?

• 35:41Speaker 01

  We've solved it both at Instacart and Tazie 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 and D team is optional. They will opt in if they have availability or interest in the topic. And so we usually end up with, you know, eight or nine people. The way I worked at Instacart was product reviews for the consumer app was me, my edge counterpart, my design counterpart, my data science counterpart, and then my senior

• 36:24Speaker 01

  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 all the time, you know, being in every meeting.

• 36:40Harry Stebbings?

  In terms of everyone being in every meeting, it seems like we've seen this kind of intensification of work culture over the last six months to a year with the rise of AI, bluntly. Have you seen work cultures change when it comes to intensity over the last five years? If so, how?

• 37:00Speaker 01

  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. But no, at 11pm, 12pm, I could ping anyone on Slack and they were already online. Like, 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 that extreme.

• 37:45Speaker 01

  But maybe what's changed is I feel like the glorification of like 996 by certain companies has been like coincidentally timed with also the AI wave. And maybe that's what makes it feel more intense.

• 38:03Harry Stebbings?

  What do you mean by that? Like, they've done it to get a better fundraising story, to be different? Unpack that one for me.

• 38:10Speaker 01

  Oh, like, why do, why would a company glorify 996? I think it's incredible marketing. It's a way of differentiating against sort of the market. Everybody's going to be intense, but we're super intense. And so like, we're going to be like Olympians and, you know, 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.

• 38:49Speaker 01

  And at the end of the day, like seventy two 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 really want to win. And so like a D one athlete feels like, oh, this might be for me.

• 39:16Harry Stebbings?

  Gosh, you've sat at the center of Silicon Valley and seen the rise and plateauing of different brands, the falling of different brands. Are there any other elements of BS culture that you see in terms of company building that you think are prevalent? You mentioned that nine nine six, great marketing, come on. Are there any other elements?

• 39:37Speaker 01

  I'm sure there are. There's a lot of things that I think are bullshit, but it's, I'm drawing a blank. Do you have any?

• 39:43Harry Stebbings?

  Yeah, honestly, for me, it's like first principles thinking. Oh, I really approached this first principles. What the fuck is first principles? Like, what does that actually mean? Like, oh, I've got, everyone has first principles and a framework. And it's just like, I'm so bored of the frameworks and first principles, which are just hollow words, which most often just lead to alignment being the answer. And I mean, when someone says alignment, take a shot, because I promise you, it means that they don't really have the answer. When people know the answer, they're incredibly specific and use data to support their argument, I tend to find. And when they don't, they discuss culture

• 40:22Harry Stebbings?

  and alignment. This focus on culture is, is actually largely bullshit. And I've learned this from Nick at Ravelute. And you may disagree with me here, so I'm very open to it, but it's, Nick only focuses on winning. He's like, the number one determinant of someone's happiness is their ability to win, development, growth, personal growth. And you grow when you win. And so I focus on everyone in the team winning. And if that happens, they will be happy.

• 40:53Speaker 01

  So the thing that like 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, you know, 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 can have

• 41:38Speaker 01

  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 slower. 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, you know, caring and trying to optimize like the culture scores and stuff like that. But it ends up, it never satisfies. So what I saw from like a poor of a like with Instacart, just a relentless focus on growth. And it works out until, you know, growth slows.

• 42:20Harry Stebbings?

  Which company had a better culture, Instacart or Thumbtack?

• 42:23Speaker 01

  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.

• 42:36Harry Stebbings?

  What could or should have been done at Instacart to make the culture better?

• 42:39Speaker 01

  I think a little bit goes a long way. We spend the first five or 10 minutes praising people for like awesome shit that they did. And I think that 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.

• 43:03Harry Stebbings?

  Is it really, really hard when the CEO transitions out or when the founder transitions out?

• 43:08Speaker 01

  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 Apurva's participation in, you know, finding and recruiting her led her to be someone of a similar pace. There's some continuity, but still like you lose a lot when the founder CEO moves on.

• 43:44Harry Stebbings?

  You totally do. Do you think Apurva was a good CEO?

• 43:47Speaker 01

  I do. I think he was remarkable at building that business. I mean, zero to thirty eight billion in valuation. That's a good CEO.

• 43:57Harry Stebbings?

  Can I ask you a blunt question? It's a commonly suggested thing, and I'm in the UK, so forgive me for this. That DoorDash beat Instacart.

• 44:05Speaker 01

  Yeah.

• 44:05Harry Stebbings?

  Do you think, do you think that's fair? And what do you think DoorDash did that Instacart didn't that led to that?

• 44:11Speaker 01

  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 win the suburbs. They got there first, beat, you know, Uber Eats to do that. And so they like won in 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.

• 44:45Harry Stebbings?

  Dude, I want to do a quick fire round. I could talk to you all day, but I want to do a quick fire where I say a short statement. You give me your immediate thoughts. Does that sound okay?

• 44:53Speaker 01

  Yeah, let's do it.

• 44:54Harry Stebbings?

  So what product leader do you most respect and admire?

• 44:57Speaker 01

  Kari at Linear. I'm going to just assume CEOs are product leaders. Kari, he's built that company on his own terms and the quality of Linear is incredible.

• 45:09Harry Stebbings?

  I invested in Linear and it's, I think, probably the best investment in Fund One. And to your point, I love how Kari has done it with such an independent mind and a huge traditional fundraising and capital efficiency. He is so good at, I mean, just a stellar, stellar CEO. I completely agree. What's your favorite interview question when hiring PMs?

• 45:28Speaker 01

  My favorite interview question with PMs is along the lines of kind of like repeated over and over. So what did you do? What exactly like did you do? And how did that like change the outcome? If I get something hand wavy, find another way to ask the same question over and over.

• 45:46Harry Stebbings?

  What's the best purchase that you've made under $500 that's improved how you live or work?

• 45:52Speaker 01

  Best recent purchase under $500 was a subscription to Whisperflow. I spend so much time writing and communicating. It's amazing. Now I have largely like stopped typing and it's really good. Like it actually like works and I can, I also don't have to edit. I can just ship it and it's returning a lot of time for me.

• 46:14Harry Stebbings?

  I have to say, I'm actually with you. I recently got it too. And the quality of transcription is second to none. And what's shocking is when you move, when you move from Whisperflow or ChatGPT's app itself to Siri or Apple products, I mean, it's unusable.

• 46:32Speaker 01

  Yeah, 100%. I'd given up on like dictation for a long time. I just didn't think it was worth it because like editing was slow and clunky. But whatever they're doing, they nailed it.

• 46:43Harry Stebbings?

  What's one thing about the future of hiring that most people don't believe or see yet?

• 46:48Speaker 01

  I think we're, for the future of hiring, where 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.

• 47:29Speaker 01

  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 recruiter. 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 roles. What's the like 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.

• 48:11Harry Stebbings?

  At what stage should a founder not be involved in the hiring process anymore?

• 48:16Speaker 01

  I think that that threshold of call it series B, it's probably not a great return on the time for a CEO or like a founder to be in every recruiting loop. They are still the pace setter, the like 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, you know, at a certain point, transition from interviewing ICs to like interviewing only management or something like that.

• 48:54Harry Stebbings?

  What did you not know about fundraising that you would most advise someone starting a company? Who's been an OG like you were in big companies before?

• 49:03Speaker 01

  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. It's very important to sort of drive towards that first like term sheet in. And then run a quick process after that first term sheet is in.

• 49:48Speaker 01

  But everything else is, I guess, kind of theatrical until that point.

• 49:52Harry Stebbings?

  When you say time box it and run a quick process, I hate that. I'm so sorry, Jason, because I'm a romantic. I want to get to know you a little bit. I'm not saying I like, you know, the high school dance where you've got 10 people and you're just picking it across. You lose all the money. This is a marriage and I'm not suggesting that it's a literal. Do you not worry that you lose personality, ability to build a relationship? And we're running a two week process. I'll open up data up on Monday, the seventh. We'll do second meetings on the 10th and we'll do third on the 14th and we'll decide on the 21st.

• 50:26Speaker 01

  Yeah, it's a, 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 fund, 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, couple of weeks and not be a pain in the ass.

• 51:09Speaker 01

  Cause like, 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.

• 51:21Harry Stebbings?

  Totally get that. And it is in our interest to preserve optionality as long as possible as an investor. I can tell you that's absolutely true. Final one, what do you know now that you wish you'd known when you started, Tezzy?

• 51:32Speaker 01

  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.

• 52:09Harry Stebbings?

  Listen, Jason, as I said, I've loved doing this. My favorite shows are when it's very much fly on the wall and when it's a very conversational flow. You've been fantastic, dude. I so appreciate you taking the time and this has been awesome.

• 52:22Speaker 01

  Awesome. Well, thank you so much for having me. This has been fun for me too.

• 52:26Harry Stebbings?

  What a show that was with Jason and I so appreciate your support for the show. If you want to find more, you can find it on Spotify by searching for 20 VC. Do leave a review or a comment there. It makes such a difference. But before we leave you today, are you struggling to beat model benchmarks or implement Gen AI in your product? If so, you need Turing. Turing is an AGI infrastructure company backed by incredible investors like Foundation Capital and Westbridge Capital. And they do two things. Number one, they help leading companies in AI labs like Salesforce, Anthropic and Meta enhance their LLMs with advanced reasoning, coding, multilinguality, multimodality and more.

• 53:07Harry Stebbings?

  Number two, they combine human and artificial intelligence expertise to deploy cutting-edge AI systems for awesome companies like Rivian and Reddit. Right now, Turing offers a free five-minute self-assessment to help you pinpoint your place in the Gen AI journey, get tailored next steps to optimize your model strategy and then finally learn how Turing can refine and implement your models for better performance. Take the guesswork out of Gen AI. Visit turing.com/20vc to start your free assessment today. As always, I so appreciate all your support and stay tuned for an incredible episode with Cohere's co-founder Nick Frost on Monday.