Deedy Das: founding team at Glean ($2.2B), investor at Menlo Ventures, and former from Google Search engineer

When the chips are down, if you think that person can run through walls and just do it no matter what, those are the guys you want to back. And it's really much less about what you think of the space and what you think of the TAM and what you think of the product. All that matters, but that matters a much, much less than do you think this person can just run through walls?

I want to give a huge thanks to our sponsor. Gelt G specializes in providing comprehensive tax solutions tailored for businesses and their owners. They'll help you and your business manage and optimize your taxes so you can pay the least amount of taxes legally possible. I'm a G customer myself. I've saved a ton of money on my taxes working with them. A huge fan of what they're doing. If you want to check it out, go to joingelt.com nextplay and let them know we sent you. They'll give you 15% off your first year. Hey, I'm Ben. This is the Next Play podcast. We're talking with folks about their careers and any learnings from it. Super excited to have Didi here with us. Didi is a principal at Menlo. He was on the founding team of Glean and had a couple technical roles at Facebook and Google before that. He's also a prolific tweeter on tech, immigration, India, fitness, and search. Super pumped to have you here.

Super honored to be here, Ben.

Thanks for inviting me, for sure. All right, well, to kick it off, I know you're a pretty, pretty active tweeter. When did that take off?

The story about the Twitter is actually quite funny. I was mostly a lurker, I would say, on Twitter for the longest time, pretty much till, you know, 2019, call it. And 2019 is when I moved to the Bay Area and coincidentally when Covid hit. So we all had a lot more free time to be online. But the real reason why I started being more regular with tweeting is the story is a friend of mine and I were out for drinks and, you know, I shared this idea with him at drinks that I had, and he sort of said, you know, you know what? Like, this is. This is the worst idea I've ever heard. Like, you. You would never say this if you were sober. Like, this is just a terrible idea. Why are you. Why are you even telling me this? And I sort of pushed back a little bit and, like, you know, dude, you have no idea what you're talking about. This is actually a wonderful idea. Somebody should go, totally do this. And he did this interesting thing where he's really good friend of mine, he turned it on Meme, where he said, you know what? You write a little bit online on blogs and stuff. I bet you would never write about this yourself. And that kind of got me thinking. You know, long story short, it got me thinking, he's absolutely right. When I thought about it the next day, the barrier to having a thought or having an opinion about something or analyzing something and actually putting it out there is pretty big, because you don't want to be associated with everything. And if somebody reads something that you've written in the past and calls you out for it, that's not a very good feeling. And I realized that when you force yourself to actually press that send button on anything, it forces you to think a little bit more deeply about whatever thought you had. It's very easy to say stuff in conversation at a very superficial level. Yeah. Oh, yeah. I read this news, and I think this about it. Like, great. But can you stand up for it over a long period of time? Can you write about it online? Can it be traced back to you? Or will people be able to judge you perhaps forever for that opinion? Who knows? And I think that got me thinking. I can think of at least one interesting thing, hopefully in a day. It's like the gym for your mind. Like, let me think about something that I found interesting. I do a lot of reading. I like to learn a lot. And it sort of serves as a mental journal for something that I found interesting over time. And it forces me to think very deeply about something without just, you know, I have a nature of playing devil's advocate without just trying to just make a point for the sake of it, but actually, like, going out there and saying, hey, you know what? This is actually what I believe on this topic, or this is something interesting on this topic that I think is valuable for people to know. And I'm not just saying it because I heard it. I did my research, and I think you guys should know about it. So that's where it took off from. And I promised myself I would sort of try to do one a day and have largely, I think, kept that cadence for the last four years or so.

And has Twitter had, like, an impact on your career so far?

I. I would say so. When I started tweeting. I always say this when people ask, ask me. It's really hard to sort of do this if you're trying to, quote, unquote, build a brand. I think some people have some success doing it. But 99 of people give up because. Not because that's like a corny incentive, but mostly because it's really hard to keep tweeting into the ether with no feedback. If you're just trying to build a brand because you just don't see results, I think you kind of have to love doing it. And because that's how I approached it, I like to believe it's over. About two, two and a half years in, I sort of saw the benefits sort of creep in where it'd be small things like some tweet would go viral and then some newspaper would write about it. But that doesn't really changed my career. Usually the way it started meaningfully impacting my career, I would say is when there would be certain people who I would probably never have imagined even meeting or being able to have the opportunity to talk to would just slide into my DMs and go like, yo, this is pretty interesting. I loved reading about it. Maybe we should just grab a cup of coffee. And I think that's where the connection started forming which don't usually immediately lead to anything but. But it makes me very insightful about what's going on. Really keeps me in the know. And yeah, I would probably be lying to myself if I didn't think it had something to do with me going into venture at least because it is at some level a game of network and being in the know.

Do you have a story about anyone you met through Twitter? Any of these folks who reached out?

My favorite one is probably Brett Taylor, if you haven't heard of Brett Taylor. For the folks who don't know, Brett Taylor is in my mind like an icon in terms of the Silicon Valley. One of the early Google, I believe he was an engineer at first. Google engineer. He was. He was known for this epic story where he apparently rewrote the entire Google Maps front end as a product manager over a weekend because he was frustrated that the engineering team wasn't doing it and he thought it was possible. So technically brilliant. Then he started, I think he started a friend feed which. Which Facebook might have acquired, started Quip, which was acquired by Salesforce for nearly a billion dollars. At some point he was the co CEO of Salesforce with. With Benioff, just a stalwart in the industry and somebody I, I admire a lot and it was just so refreshing. He called me, you know, he DM because I tweeted about this research paper or the early days of LLMs and breaking down this research paper and what I thought about it and I still remember he sort of made middle of my workday just pings me with a oh, interesting tweet and had a question about the research paper. Like I wrote it. And I remember just being like, okay, drop everything. I need to answer Brett's question because this is the most important thing in my day right now. So I gave him a thoughtful answer. He eventually was like, hey, love to meet, let's grab some time. And we spent an hour just talking about, you know, his experience, his views on tech. And I just thought it was his clarity of thought on how to do things was so remarkable because especially in the day we live in, I think a lot of people can say things that are true sounding or perhaps true, but they have no conviction on it. And then when someone who's been just doing it and living it for so long says something even kind of generic sounding, you can just tell when you ask him a counter question, his reasoning and his insight is just immaculate. Immaculate. Even though the thing itself might not sound groundbreaking, when he talks about why he thinks that and examples, it's just, you know, this guy just gets something that most people don't. So I think that was one of the ones I really liked.

Super cool. So I want to jump back into your career. A lot of operators, you know, the most important decision they make is what company they join. And I know you did a great job joining Glean. Last valuation was 2.2 billion and, you know, growing fast. How did you choose to join as a founding engineer? Like, why did you pick Lean Man?

Ben, I don't know what to tell you. Like, I got really lucky. Well, it's. These things are super hard and I think if, if you've been in the Silicon Valley or in the tech industry long enough, I think most people would say, look, there's at that level of startup, there's 90% who you of those startups at that stage which are probably not great. And you'd probably be like, yeah, probably not joining this. And then there's 10% where you'd be like, it's anybody's guess. And maybe, maybe not. We'll see. And I think Glean, probably even at the. It was called co before that, before it was called Glean Scio, Terrible name, but it was called that before. I would put it in that top 10% category of good founder, great, strong teams, but who knows if it'll be successful. I took a bet on it and it turned out that it worked. The things that I would say is one thing that definitely usually doesn't work. Is when you join a company after the hype is already there. For me, it was purely based. The decision was purely based off of first principles thinking. And that's not that fancy. Like it's really, really basic stuff. I'd met a bunch of startups at that point of varying stages. When I met Arvind, I thought, look, this guy's a second time unicorn entrepreneur. He started Rubrik, he scales Rubrik, which is enterprise SaaS business. That's number one he's managed to hire already. Like the first initial team. Brilliant, brilliant. People like these are not just young ambitious new grads, but it was tenured people who were taking a significant financial risk by leaving their cushy job at what, what, what have you company to go out on a limb to start this, which gives me a lot of conviction. The third thing is, Arvind, Enterprise SaaS is probably not the sexiest business in the world, but the reason people do it and the reason I have confidence that it's more repeatable is it is fairly low risk when it comes to things in tech. It's one of the lower risk things. And the fact that he'd done enterprise SaaS and was trying to do it again is better than if you were doing to like a consumer social media app and trying to do it again. Those aren't less repeatable playbooks, I would say, than Enterprise SaaS. So those were three of them. And then the biggest one was I was always sort of a nerd about search. Search was a problem space that I just thought was so beautiful for so many reasons. It covers various aspects of computer science at Facebook. That's one of the things I love doing. I moved to Google particularly to do search. I told them the only way I would join was if you gave me a team in search. I just love the idea that you have information retrieval, machine learning, natural language processing, distributed systems, all packaged into this really like neat, beautiful ui. And it never is perfect. It's just this idea of using technology to answer questions and it's a never ending quest to get better and better and better. And so I loved search and this was just enterprise search. So the real question I had to ask, the real doubt in my mind was not was why hasn't this been done before? Why is this the right time? That was the main question I was asking. And after a lot of back and forth, look, there's no perfect answer. But I was satisfied with where we landed. Like, I was like, okay, here's some things the companies before didn't do. Here's some things we will do. Here's the edge that we have on a IP technological basis to win that market and we believe that market is worth winning. Like it's a big, it's a big need for people. So all of those things said and done, I was convinced that this was good enough reason to take a bet. And then the downside case is, look, if it's not working, we'll know in one or two years that it's not working and we'll go do something else. It's not the worst thing in the world. The opportunity cost of not doing it now felt high enough to just jump into it. So that's a long answer to why, why I picked clean.

What do you think your like your conviction rate was before joining from, from 1 to 10, 10 being, you know, super high conviction.

I, I could tell you this when I, I still read this journal entry of mine where I'd written what I think will happen to CEO. You know, what are the outcomes that, that I would be happy with, not happy with medium, whatever. And I said my best case outcome, top 1% outcome is this becomes a unicorn company in five years. And that happened in, in like three and a half years. So it clearly exceeded my expectations. And I thought my medium case was I thought it will get to series B, you know, get to series B, maybe be languishing at that point. So, you know, whatever level of conviction that equates to, I would say probably like a six or a seven, it's not very high. It's like, I think it's insane if you say you have a conviction level 10 startups have risk. Like you just, you still take it if it's, if it's a 6, most startups, the baseline is of 0. So.

So and sounds like you were, you were evaluating other companies around the same time. Are there any specific reasons that you decided to stick away from certain companies? Like what were those, you know, what were the factors that kept you from joining other, other companies at the time?

I'll talk first about companies that are not really apples to apples. So I would say mid stage to later stage. The more I spoke to mid stage to later stage companies and this is hopefully not a knock on those companies, but it became abundantly clear to me in those conversations that the reason that the people were there were less about the passion for the technology and the problem and more for the obvious reason that they thought they were going to get really rich when this company ipo. And that's a typical attitude I See, in a growth company, and I would kind of joke about this, and I know some people, Stripe is a phenomenal company. It's going to do really well. One of the companies I was considering at the time, but I would joke about this where I'm like, you act like you're really passionate about payments, but are you really passionate about payments or are you just at Stripe because you know it's gonna 10x in the next three years. Right. And that made that sort of. It made me realize, look, if that's what my goal is, then Stripe is a great company. It has some great talent, it's building for an important problem and it's probably gonna make a lot of money. But the brand is already built, the product is already built. Everything you do is just incremental. It's not that different from joining Google. And that's not what the experience I wanted. So I felt that way. I mean, Stripe is sort of a, I would say my metaphor for a lot of these growth stage companies. The ones that you'd consider joining the brand is already built and they're still trying to sell you to come join them. But it's, it's a different job. You're riding a roller coaster that's riding a rocket ship that's already taken off. You're not building the rocket ship. And I wanted to build the rocket ship and from nothing. And, and so I wanted to stick to companies ideally below certain size or stage. And then of the companies in that layer that I spoke to, there's just so much noise and it's hard to evaluate. I left, to be very honest, I left most of the conversations thinking, this guy could be right. He seems pretty smart. I just don't know. I just don't have enough information to evaluate what he's saying. He's clearly perfected the sales pitch to a candidate because that's what his job is. But I just don't know enough about that space to comment. And I felt a lot of conversations, most of them were ended with I don't think this team is strong enough for me to genuinely respect. And I don't feel like I know enough of the or. I don't feel I know enough about the space to have any conviction, yes or no, whether it's going to work. So the only company that met those two things were lean at the time.

That makes sense. And do you remember what your first week or first few weeks at Glean looked like?

Yeah, absolutely. When you join a company that's like under 10, people just so small. And we were working in this, basically an unused Kleiner office at the time, one of our investors is offices that they'd abandoned. It was the most stark things for me was how little people cared about the bullshit around, around a company that I'm so used to, like, oh, this is a process and oh, I have to like go home and do this and oh, like, yeah, schedule a meeting with me. Everything was, it just felt like I was transported back to college, but everyone actually knew what they were doing. It was back in college, but people who had been working, most of them for 10 plus years at the time, who knew exactly what they're doing, no nonsense. And it's not like we didn't have fun. We had a lot of banter and laughs and jokes. But when we were working, we were working. We were all laser focused on building this thing. And the conversations we'd have were just like, hey man, we're gonna make this huge decision, but we're gonna make it in the next 10 minutes or on your, at your desk. So what do you think about this? So let's talk about it. And then just constant like lobbying ideas by each other, but so aligned in what we wanted to achieve because we all knew that this is, means nothing unless this works for all of us. So that sense of being as a part of a team just really shined in that first few weeks. And then I felt like complete imposter syndrome, of course, like completely overwhelmed at just the speed at which these guys moved. I thought I moved pretty fast at Google, but I was like, man, I don't know if I can, like, I don't know if I can even at my best, be as fast as you guys. Eventually I think I got better. So just speed of execution, rigor, and a knowledge of things outside the company. Google was very insular. So as long as you knew like five, six systems inside, you were still considered pretty good. Here it's about keeping up with what's going on outside. Like, what are the tools that people use, what are the libraries, what are the technologies, what works, what doesn't work, having an opinion on that, and just the ability to sort of be. This is technical jack of all trades for a lot of people there felt like that. So yeah, I just thought it was a lot of imposter syndrome. But I learned so much because I felt like the, the dumbest person in the room.

And who, who was your manager when you joined and how did you decide what to work on?

Completely flat hierarchy. We all reported to the CEO no management, nothing. None of the, none of the, I don't want to call them BS one on ones but like, you know, half the one on ones people do at companies are just like what do you actually talking about? So most of it was, yeah, we were all working on pretty much everything. I remember my starter project for the first few weeks was okay, we've built all this, we built some of this enterprise search like a basic version but the only way we can deploy this is on command line. So figure out how everything connects. All the different tools connect to enterprise search and the setup flow. And that was so crucial to get new customers on board. And that's like not, it's not an onboarding project, like it's not a bug fix. This is kind of a critical thing and sort of, yeah, we kind of naturally organically picked these big areas. I worked on various parts of the stack over time, but there was no management structure. And it was, it was very organic how we decided to work on what kind of based on interest, kind of based on fit and ability. Usually with startups there's a lot more work than there are hours. The only critical decisions to make are sometimes you have to be like, okay, that is just not important to work on. So let's just can that. And then people just sort of organically find their fit and go work on things that are important.

Do you remember at what point the flat structure changed?

Yeah, there. It took a long time intentionally I would say I think it's about 50, 50, 50 plus people where the flat structure changed. I want to say about two years in, but I might be getting that wrong. The flat structure is just doesn't scale with people. It really only works when everyone knows each other, everyone has a friendly relationship and everyone has all the same incentives. And as a company grows, I think the natural sentiment of ownership and then the incentives are different for people who joined a company four years in and versus one year in when you don't know, you don't know everybody. So you can't really make the same dynamic work at its stretch. I like to call it like, you know, in a small, highly performant group you can do basically what is socialism, which is everyone all for one, one for all. We're just all on the same team. But over time you need these functional units, you need structure, you need like a sort of structure where you're like, you're responsible for that and we'll see how good you are at that. And if you're not, we'll figure something out and that's, that just happens naturally, this sort of capitalistic structure as you scale and that was about 50.

Got it. And, and at some point you switched to being on the product side. What was that transition like for you?

One of the side effects of the way startups scale and all startups, I think go undergo growing pains is not only the sort of mismatch in incentives and different sort of profiles I said before, but a lot of the younger, the early people naturally become managers of some team, as did I. And unfortunately people who love building products from zero to one rarely love management, no matter what they tell you. And I think I was probably in that bucket, which is I could do it. I wasn't, I don't think I was terrible at it, but I didn't love it. Like it's basically a task manager type job. Like you're managing people, you're always context switching, you're not building anything. It's not much creative work. It's really responsible work, like making sure people do their stuff, you handle the gaps and then you just do the same thing over and over and over every single day and make sure everything is in place. That didn't work for me for too long. I was sort of feeling like, you know, this can't be it. Like I can't be doing management work forever. I don't get much joy. And very naturally, I think towards the end of 2022 is when a lot of the LLM stuff started getting really good. GPT3 sort of took off. People were talking about it, I was playing with it and building stuff on the side with it. But it became so apparent to me then that we couldn't survive as a company with the mission of helping information at work if we didn't integrate LLMs into our flow. It just wouldn't work. It was a critical new technology that changed the game. And so we did a whole push. I was a part of a couple of people who did a whole push to say, hey, we need to build something here. So we built a prototype and we fought this like sort of internal startup battle where we were like, okay, this is going. This is bigger than just this. This is not just a prototype. And we eventually made it a second skew, a second whole product line that we were going to sell. And then I sort of naturally realized, look, I had a choice here, I could stay. I sort of shift my from my previous response position to leading this new product as an engineer or I could just be the, the product lead. And I realized that I wanted to Lead the product. Like I had so many opinions, I just really didn't trust anybody else to do this job. And it wasn't like, oh, I wanted a career transition and I wanted to be a pm. I never really wanted to be a pm. It was really in the moment. I thought given the roles that we had and the people that we had around the project that I think I was best suited to doing the product side work and not the engineering side work. There were enough people that were pretty good at the engineering, not the people I thought could really drive this product forward. And that's how I made that transition. Eventually that product did really well, I think. We launched mid year that year. So we started development in like Jan. Feb. We launched in June and by the end of the year it was more than 25% of like the company revenue. So it grew really fast and it was a, I would say a pretty good success.

Amazing. It seems like you had a really great run there. What was leaving like it must have been pretty challenging.

Yeah, it's always tough. You know, you, at the risk of sounding cliche, like it is hard to sort of almost break up with a family that you've built these really strong. It's not that you just worked with them for four years. Like you went through a lot of emotional stuff. Like you know, clearly when you work on a startup, like 80% of your hours are going in here and you ride those waves of bad quarter, good quarter, bad time, good time. And so you form a natural bond with people. We're like, yeah, we went through this shit together and so it's always hard to leave something like that. However, after four years I genuinely felt like similar to how I was feeling with management. I just wasn't enjoying the, the one to end journey as much as the zero to one journey. A lot of my days started feeling extremely repetitive. More of the same. I like to. I forget the exact quote but Frankman talks about it in his. He's a great, great operational executive in his book where he kind of alludes to this fact that good execution is a lot of showing up and doing the same thing over and over and over and over again. And that's what it looks like. It's just really boring and repetitive. I just didn't love that. Like it less creativity, a lot of hours, a lot of responding to a lot of people pinging you on slack meetings and just not having the time to do great creative thought. Just pure execution. And that I could do for a while. But I thought, look, this is Just not the best use. I thought of my time and my interest. Let me just try something else for now. I think I've gotten what I needed to get out of Glean and I really liked it. Maybe I come back to it at a later point, but I just don't think it's the right time to get into that execution mode.

Yeah, that resonates. I had pretty similar feelings leaving Notion. I think very similar trajectory and you.

Know, and Notion's a great company and so it's hard. I mean, I'm sure a lot of people ask you like, hey, why would you. You leave such a rocket ship.

Yeah, well, I would probably tell them a lot of things you just said. So I know you recently joined Menlo Ventures, so you switched to the Venture side. How did that happen? Did you always want to be in Venture?

No, I. If I think if I wanted to be in product or in Venture, I would probably more strongly consider going to business school and take a very different route to it. At its core, I like building things and being creative. That's just what I love to do. And I wouldn't want to be in a position where I couldn't do that. The reason why I moved to Venture is because after my run at Glean, I was sort of thinking of what are the next steps that make sense. I didn't really want to go back to a big tech company and sort of just coast or just work on a problem and you know, in the middle of an island, in the middle of nowhere. I thought of my options and I. It felt like the top two options that I really considered strongly was to start something of my own or to join Venture. Starting something of my own obviously has its own trade offs. A lot of work, a lot of commitment. For a long period of time I wasn't. I had a lot of things I wanted to start, but I wasn't ready to make that commitment. I thought I needed to frankly just settle my personal life and have more stability there and get like married maybe and then just have some stability there before I felt like I was ready to take that risk because I see it as a five to seven year endeavor of basically doing nothing else but work. And that's a, that's a lot of commitment. To sign up to Venture I thought was interesting because there's a couple of things that I really liked about it. I thought, hey, you know, why aren't there more tech people in Venture? And it turns out there's the reason there aren't more technical people in Venture. Is because most technical people would tear their hair out by doing this job. It is just a lot of meetings, a lot of fluff at times and a lot of, you know, hypothesizing about things while meeting people and not really doing stuff. For me, I actually enjoy meeting people and being social. So that, that worked in my favor. I wanted to be very close to startups and see the 0 to 1 more, get more reps on the 0 to 1. And I didn't know a better way to do it than to sort of be in venture and see multiple startups undergo that journey. So those are two of the reasons. The third thing is I genuinely think that on a more philosophical level, I think there should be more technical operator type people in venture. I think it is, I think it's. If I was a founder I would, I would lean more closely to wanting to be, to partner with an investor who understood my business at a much deeper level and who could sort of speak the language I was speaking. So I wanted to just be that person on the venture side and not to say there aren't other people like me, but I think fewer. And so that was sort of my angle into it.

And so how did you end up specifically at Menlo Ventures? Like what was the process to getting there?

There were, I did consider more firms. Like I was talking to a bunch of firms. And the main things that I realized when I was talking to various venture firms firms is a couple of things. The first and most immediate thing I realized is what founders think of firms, unlike tech, unlike engineering, what founders think of firms from the outside are very different from how firms are on the inside. And the incentives, the dynamics, the politics, the culture are extremely hard to find out unless you really talk to people. And so firstly, you have to do a lot of that. So you have to do a lot of understanding what you're really signing up for versus just what the external perception is. Whereas in tech it's sort of understood like Google, you'll get this, Facebook, you'll get this. People sort of get it. So that was number one when I did all of that. The things I really liked about Menlo is, look, it's been around for a really long time. It's one of those older firms that has maybe not had a lot of time in the sun. It's, it's not one of those, you know, household names like Sequoias, but it's had a good 48 years, which is way more than, than most funds. It had 16 funds. And usually if you look at the number how likely a fund is to just go to zero. Having 16 funds means that whether people write about you that much or not, you clearly doing something right. So that's number one, good track record. Number two, I like the fact that it, it there was something to be built at Melo. Like it's not one of the things that I heard a lot not to name names, but if you join the best firm out there, it's all about the firm and less about. About what you can make the firm. It's already the best, what are you gonna do for it? You're just joining a nice umbrella. And I like the fact that Menlo still had some rung to climb. It had an ambition to do more and I could be a part of that journey. So I, I like that. And number three, I think the culture super collaborative. I think compared to most, a lot of other firms, at least that I spoke to. Number four, much more, much more diligence when doing deals. A lot of firms, you can't tell from the outside, they love to spray checks. Look, if you're going to write tons and tons of checks, then you can look like a genius in retrospect because you can just point out one of the hundred checks you wrote and been like, I'm so smart. I called that. Like no, you really didn't call that. You called 100 of them and one of them happened to be pretty good. So I don't think Menlo operates that way. Which means there is still a, like an actual art of picking involved. Not to say all firms are like this, but a lot of firms are. And then lastly, it was really important to me to work with a, with somebody who was also an operator and technical because I felt like I couldn't be the only one. It would just not work. I would be running, running up into a brick wall. So two of the technical investors I respect most in the Valley are, you know, Quentin Clark at General Catalyst, who's on our board at Glean. Absolute powerhouse. Ex CTO of Dropbox, ex CTO of SAP, you know, one of the CVP's of Microsoft. Great, great guy. I would, I would definitely love to do that. And then the other one I thought was amazing with an equally equal caliber is who I work with now is Tim Tully. And Tim, the ex CTO of Splunk, Tenured, you know, engineer turned investor. And what really struck me about him was so passionate about the craft. Like, despite being a vc, like you should see that how much he codes, he'll just I would not expect a 50 year old dude who's, you know, for by all practical purposes or not, he's not 50. He would give me a hard time for hearing that. But like near 50 year old guy who is fit beyond belief has, you know, he could retire if he wanted to. He's made all the money he needs to, but he'll show up on Sunday in SF to be at a hackathon full of, you know, sweaty college grads being like, dude, I just love this and I like, I love that energy. And I really resonated with, with that. So that's one of the reasons, those are all the reasons that I thought Menlo was.

Is anything that surprised you so far.

About Venture or about Menlo?

Yeah, yeah.

In this new role, it surprises me how much when you have very few signals. Even the VCs who've been very successful over a long period of time, they can't outwardly say this to founders or say this publicly. There's a lot of things you just cannot say publicly because it looks a bad look, like it makes you look snobby and arrogant and you don't want to be like that. But at its core, when you're doing early stage investing, a lot of that decision is judging the person. And that is an imperfect art. Like no one's going to get it always right. It's an extremely subjective matter. And I think that's the part that surprises me most where as an engineer, it's just obviously not intuitive for me. Like I like things that have objective yes and yes and no. Like there is a right answer here. And the craft of Venture, the more people I've spoken to who have done this for like multiple, multiple years have been on the Midas list multiple, multiple times. The guys who've been doing it for two, three decades almost always are like it's about reading the person. The only thing I can tell you about multiple eras of tech is the only philosophy that doesn't that works is when the chips are down. If you think that person can run through walls and just do it no matter what, those are the guys you want to back. And it's really much less about what you think of the space and what you think of the TAM and what you think of, of the product, all that matters. But that matters a much, much less than do you think this person can just run through walls? And I think that was surprising to me how much that mattered in Venture.

So before we wrap up, it seems like you've had an amazing run. So far in your career. And I'm sure a ton of people reach out to you asking for advice. What do you usually tell them?

Very generic stuff. I mean, I generally believe this. I think the number one, there's a framework to sort of thinking about, I think your career, in your life. And number one is to figure out what actually matters to me. A lot of people lie to themselves about what matters to them, so they make stupid choices, but what actually matters to you. And it's okay if money is the only thing that matters to you, Just say it. Like, just be honest with yourself at least. So figure out these things that matter to you. The hardest part about doing that is you also have to rely on, I think, people older than you and knowing how those things are likely to change over time because you don't want to make a point decision. So figure out what matters to you and is likely to matter to you. And then the second step is figure out what you're actually good at. What are you, what do you like to do? What are you good at? What energizes you in a very genuine way. And if that answer is like not much, then like, be honest with yourself. Like, look, this is just who I am. It's not much. And I think once you have those two layers down, then it's really about picking the career that fits your needs. I don't think there's a one size fits all sort of advice for everybody. And I think a lot of people get really unhappy because they want one size fits all advice without being very honest to them themselves about what they want. And a lot of people, and the most common one is a lot of people just want to be seen as successful. This is what I see the most. This is, I think the, probably the problem I see the most. And it's not like I don't want that either. Everyone wants that. But if that's the only thing that drives you, often the decision making you do to get there is always going to be a lagging indicator. It's just a bad framework. If you only want to be seen as successful, you will only join things after they are already seen as successful. You're never going to take a risk. And I think that's the most common mistake people make in their careers is just not trusting their gut one and then just not being honest with themselves about what they want. I think that's, that's sort of the framework I established. And I, you know, you see this so many times like common, common problems or mistakes people have made in Their career are. I've seen extremely good engineers move to product because they thought it was a more exclusive role. And then they're like, I don't like this, it's just not a good job. And that's a, that's a occasion where you should have just been honest with what, what do you want to do Instead of looking at what's seen as a certain status or exclusivity, just ask yourself. That's, that's sort of the advice I would give a lot of people. I get a lot of themes of the DMs that hit my inbox and a recurring theme that I hear a lot is of course, you know, how do I get a job and how do I get into tech in general, how do I get into product? And then of course, how do I, how do I get into venture? And I would say that even in the first sort of, I'm very early days, but in the first month of doing this job, I genuinely think that it's a big mistake to sort of view venture as this glamorous job that you can be in so you can, you know, fund different startups. The truth of the matter is Venture is a really, it's, it may not be the most stressful job on a day to day basis, but it's a, a short term gig. You know, most people, including me, I might just only make it here two years before they realize I'm not doing, I haven't done any good deals and then I'm out. And that's just the nature of the business. Number two is it is a gig where none of the INF inputs correlate at all to the outputs which can be very jarring for people who are used to that being true. A lot of high achieving people are used to that. Like if I put in eight hours of work for this final, I'll probably do well. If I put in two, I probably won't. In venture you can put in 20 hours of work for put in like 60 hours of work a week, you might not do well. Somebody can put in 10 hours of work, but they might be better than you because it's really about, did you find that one company that had an outlier outcome more than the process? So that's another thing to note on a day to day basis. Even though it's not stressful, it is incredibly time consuming. And if you are a person who likes, you know, generally the idea of work life balance, generally the idea of I want my day to end at 6 and do something on the evening and then sort of turn off until the next day. This is just not the right gig for you. You are going to be always on. You're going to have 20 unread emails and on all times that you're gonna have to respond to. Your day is filled with meetings, meeting, meeting, meeting almost every day. You're going to have zero time to process your thoughts. And somehow in all of the gaps that you have, you have to keep up with the industry all the time to know what's actually going on, learn about new startups, know what's out there and constantly be on and in the know. So it's not a fun industry for everybody. I genuinely only recommend this for people who just truly like, I don't know, live and breathe tech and just want to, want to be, you know, all in on doing this all the time. And if you, if you enjoy that, I think it works really well for you. And if you're looking for a gig where you want to play golf and, and have high prestige, I feel like this is not the right one.

Thanks, Didi. This has been super helpful and insightful and really appreciate taking the time to come on.

Of course. It was really, really great chatting with you, Ben. I would love to obviously go for one hour longer if we could next time.