Cold open
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, cofounder 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,
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Conversation
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. Yeah. Really happy to be here. Thanks for having me. Now I wanna start a little bit before Tezi, and I wanna 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?
Biggest product lesson learned from Instacart was as much as AB 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 40,000,000,000 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, 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 4,000,000,000. 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 5,000,000,000.
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.
So how I translated that into Tezi, 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 the needle on our ability to have a differentiated positioning and to, like, market ourselves.
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?
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 at Tezi. 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. And so I think of it as kinda like one swing, and I wanna finish the swing. But in between, we will need to involve customers if we lack certainty.
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 has it changed with AI? 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. 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 gonna 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.
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 Eng who still has 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? 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 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 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.
Do you think early stage companies do need PMs? It’s always been held 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?
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.
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?
I think where PMs spend their time will evolve. And by that, I mean, instead of long PRDs and, like, 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’s we have already built versus new capabilities? That requires 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.
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?
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.
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 bets that are based on, like, sensible, secular, long term trends or, you know, otherwise.
Do you think you should have a decision making structure where people are able to make decisions fast versus seek consensus and debate? 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.
What’s the biggest nonconsensus product decision you made that didn’t work, and what did you learn from it? I
think the biggest nonconsensus product decision that I made that didn’t work is how we built Daisy, like the v one. 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 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 and or opening a role all the way up to the point where you’re ready to extend 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 wanna 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, 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 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.
How do you know whether something’s full build or MVP a bull? What’s that difference between the two?
For us, it’s about the thesis that we’re trying to test. And in order to be able to validate or invalidate, you know, 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’re 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 breath of a human sort of role. And so for us, that necessitated, like, building more.
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, 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 that, like, hey. If we’d only focused on sourcing or only focused on an initial core segment or wedge. When we spoke before, you said something that I I really liked.
You said most hiring managers hire poorly, And I 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. Okay? So what are the most common ways that people screw it up?
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.
But most hiring managers think that they’ve outsourced it, they are hands off, and it doesn’t go well.
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 these values, the skills? How do I know?
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. I’ll put it as a JD, post it.
And I just really need to start talking to people. For me, I I learned through talking to the first twenty, thirty candidates to get a feel for at least some pattern matching across them of what is 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.
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?
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, 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.
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?
I’ve learned a lot about interviewing from Apoorva, 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 100 questions for him. He’s, like, one question for me was, like he 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 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. 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.
Do you think fundamentally it is so competitive to say 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.
If I think about the founders and experience sort of veteran, like myself and my cofounder, 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.
You mentioned the fifteen hours a week that the person from Slack partakes in with you. How do you advise founders on part time advisers in that respect, which you see more and more of?
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 cofounder’s background. But by and large, I find advice to be, like, cheap. I I 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. 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 wanna sign on full time to, you know, do a fifteen, twenty hour a week, like, PM job.
And it’s been remarkable, actually. So I I’ve worked with, a 100 PMs probably over the course of my career. I like his fifteen to twenty hours more than most of their, like, fifty to sixty hours. What?
Why? What makes it so successful in a way that founders can learn from?
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. 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.
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?
Yeah. I’ve seen this movie, you know, many companies over the last fifteen 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 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, 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 gonna get it through somebody else.
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?
I’m gonna 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.
Do you think most CPOs are shit?
Yes. Yeah. Absolutely.
Yeah. How do you know how do you know if a CPO is shit? Like, I I interviewed all the CPOs. How do I know if that shit if they say alignment a lot? Like, what are the buzzwords?
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 gonna 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. It’s not hand wavy. It’s not platitudes. It is, like, a clear or 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 slight of hand to say, like, hey.
We’re gonna do this, and we’re gonna 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, like, really is the CPOs to own.
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?
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, you know, 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, and I wanna spend as little time on it as is, like, necessary to achieve the end, which is, you know, shipping great product.
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?
I think the timing for value extraction 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 for a dime,
and so don’t do that. It 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.
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.
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?
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 than, 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 coach right, they will bring it at the right times, and it will be a help, not a hindrance.
What do you mean push not pull when it comes to product reviews? Just
so I understand that.
Yeah. So for Tezi 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 tick 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 ENG.
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, and I want to, like, make sure, you know, it’s on track.
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?
We’ve solved it both at Instacart and Tezi with basically required versus optional attendees. So project team, opts in. They invite themselves. Required for us right now is me and my cofounder. 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 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 all the time, you know, being in every meeting.
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 at Bluntney. Have you seen work cultures change when it comes to intensity over the last five years? If so, how?
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 sixty, seventy hours. A bad week is a 100 to a 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, but maybe what’s changed is I feel like the glorification of, like, nine nine six by certain companies has been, like, coincidentally timed with also the AI wave, and maybe that’s what makes it feel more intense.
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.
Oh, like, why do why would a company glorify nine nine six? I think it’s incredible marketing. It’s a way of differentiating against sort of the market. Everybody’s gonna be intense, but we’re super intense. And so, like, we’re gonna 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, twenty to twenty six 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, 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 wanna win. And so, like, a d one athlete feels like, oh, this might be for me.
Gosh, you 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? 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?
Yeah. Honestly, for me, it’s like first principles thinking. Oh, I really approach this first principles. What the fuck is first principles? Like, what does that actually mean? Like, oh, I’ve got everyone has first principles in 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 and alignment. This focus on culture is actually largely bullshit. And I’ve learned this from Nick at Revolut, 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 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.
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 gonna have cultural sort of issues that, you know, make it kinda 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 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 slower. The culture amp surveys get worse in terms of their score. 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, Apoorva, like, with Instacart, just a relentless focus on growth, and it works out, until, you know, growth slows.
Which company had a better culture? Instacart or Thumbtack? 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.
What could or should have been done at Instacart to make the culture better?
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.
Is it really, really hard when the CEO transitions out or when the founder transitions out?
Yes. Yeah. Founder transitions, really hard. I think Fiji did it really effectively. She 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 Apoorva’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.
You totally do. Do you think Apoorva was a good CEO? I do. I think he was remarkable at building that business. I mean, 0 to 38,000,000,000 in valuation, that’s a good CEO.
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. Yeah. Do you think do you think that’s fair? And what do you think DoorDash did that Instacart didn’t that led to that?
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 their 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.
Dude, I wanna do a quick fire round. I could talk to you all day, but I wanna do a quick fire where I say a short statement, you give me your immediate thoughts. Does that sound okay? Yeah. Let’s do it. So what product leader do you most respect and admire?
Kari at Linear. I’m gonna just assume CEOs are product leaders. Kari, he’s built that company, on his own terms, and the quality of Linear is incredible.
I invested in in Linear, and it’s, I think, probably the best investment in Fund one. And to your point, I love how Harry has done it with such an independent mind and issued 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?
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.
What’s the best purchase that you’ve made under $500 that’s improved how you live or work?
Best recent purchase under $500 was a subscription to Whisper Flow. 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, like, works, and I can I also don’t have to add it? I can just ship it, and it’s
returning a lot of time for me. 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.
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.
What’s one thing about the future of hiring that most people don’t believe or see yet?
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 works 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 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 rules, 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.
At what stage should a founder not be involved in the hiring process anymore?
I think that the 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 pacesetter, 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.
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? Mhmm.
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. But everything else is, I guess, kind of theatrical, until that point.
When you say time box and run a quick process, I hate that. I’m so sorry, Jason, because I’m a romantic. I wanna get to know you a little bit. I’m not saying Yeah. I like, you know, the high school dance where you’ve got 10 people and you’re just picking across, you lose all their 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 relationship? And we’re running a two week process. I’ll open up data rep on Monday the seventh.
We’ll do second meetings on the tenth, and we’ll do third on the fourteenth, and we’ll decide on the twenty first.
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 gonna 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 weeks and not be a pain in the ass because, like, we wanna 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.
Totally get that. And it is in our interest to preserve optionality as long as possible as an investor. I I can tell you that’s absolutely true. Final one. What do you know now that you wish you’d known when you started Tezi?
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 gonna 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.
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.
Awesome. Well, thank you so much for having me. This has been fun for me too.
What a show that was with Jason, and I so appreciate your support for the show. If you wanna 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,
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