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Success Story with Scott D. Clary
Tim Guleri - Legendary VC & Tech Founder with Multiple IPO Exits | Building Billion-Dollar Tech Companies
01:23:49
Tim Guleri is a seasoned venture capitalist and managing partner at Sierra Ventures, a Silicon Valley-based early-stage technology-focused venture capital firm. With over two decades of experience in the technology industry, he has a strong track record of identifying and nurturing successful startups. Before joining Sierra Ventures, he co-founded Scopus Technology, which went public in 1995 and was later acquired by Siebel Systems for $460 million, and Octane Software, which was acquired by E.piphany in 2000 for $3.2 billion.
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- [00:00]
Tim Gulari
So when I look back at the journey from Virginia Tech, where I came from a master's, I lost my scholarship. I'm like, I'm not going back to that. I'm just going to sell books door to door. So that then led me on to my first entrepreneurial job and then I ultimately started Octane.
- [00:15]
Scott Clary
How does a man go from selling books door to door to selling his company for $3.2 billion? Today, I sit down with someone who did just that. Tim Gulari started with Hustle, an engineering degree, a master's in robotics in a side gig selling books to fund school.
- [00:28]
Tim Gulari
When I started Octane in 96, shipped in the was, the Internet was happening and I was confident that the Internet's going to once again change the customer interaction sort of landscape. That was my insight as an entrepreneur and that's how I built the company.
- [00:42]
Scott Clary
In the 90s, he helped build Scopus technology, sold for $750 million before founding Octane Software. Now as managing director at Sierra Ventures, he's backed billion dollar exits like Sourcefire, Shape Security and Treasure Data. This is the Tim Gulari story.
- [00:56]
Tim Gulari
Nothing great gets built overnight. You have to have the courage as an entrepreneur to realize that and lean into that commitment. And then we of thought partners and capital partners to kind of take you through that journey, have a pretty deeply ingrained view on what a great venture partner is. Early stage of the company, which is giving you the gift of time.
- [01:19]
Unknown
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- [05:24]
Scott Clary
Tim, you've gone from selling books door to door to putting yourself through grad school to building billion dollar companies. So talk to me about a common threat in your journey.
- [05:35]
Tim Gulari
I think, Scott, the common thread, I would say, is that, you know, you as a, when you're growing up, as a child or whatever, you have certain, you know, sets of trainings that your parents impart on you and that tends to shape you as an individual. And for me, when I look back, because I've reflected on this many times, I think there were two things. One I got from my dad, the other from my mom. So my mom was an avid gardener and she loved, you know, literally she had a patch of dirt that she'd given me that was my, my patch of dirt and you know, I was responsible for it. Get my hands dirty, make sure I, you know, I kind of water the plants, all that good stuff. So the idea that you're constantly working if you love something and then it doesn't feel like work, right? And the idea that you're, you know, constantly pushing the ball forward, right, is, is, is one key anchoring attribute, I guess I have. And the other one is my dad was in the Indian army when I was growing up. He always, you know, and then he was the infantry, so life was pretty hard. And he always had this term called box on, you know, which is, you know, when you're boxing and you fall on the ground, the referee says, you know, once you count you down, he goes box on. Okay, you get up and you keep going again, right? So point being that obviously you have to be smart at your skill set and, you know, technical or other ways, but once you kind of have some liftoff, you gotta go back to your kind of core, you know, features as an individual, what makes you, you, right? So when I look back at the journey from Virginia Tech where I came for my Masters and then, you know, one supper, I lost my sponsorship scholarship and so instead of calling dad for money, I'm like, I'm not going back to dad. I'm just going to sell books door to door and earn, you know, 10, 12 grand and pay my tuition for the next quarter, which is the door to door selling that I did and actually in Sacramento, California. But it was one of those things where you fall down, you know, adversity happens, but you just kind of pick yourself up and keep going. Right. And so that then, you know, sort of, you know, led me on to my first entrepreneurial job. And then I ultimately started Octane, which is the company you're referring to, which had a great outcome.
- [08:01]
Scott Clary
So when you think about entrepreneurship and you sort of, you discovered, I think that you discovered when you started selling books, maybe it was earlier than that that you had this entrepreneurial mindset. And I've always gone back and forth on this idea and different people had different opinions like, can entrepreneurship be learned? Is it something that you're born with? Is it something that you learn? What do you feel? Do you feel like it was something that you've always been or was it something that you had to work for?
- [08:29]
Tim Gulari
No, I think I'm on the camp where it can absolutely be learned. So if you look at my history, I didn't come from a business family. I came from an army family where dad got fixed income, right. And he went from, you know, worked from like a very regimented, like 8:30 in the morning, back at, you know, 4:00pm and then off to, you know, his evening activities. So growing up, I had no business, you know, being talked around the table, none of that. Right. But I think going back to the, you know, the what made me me, interestingly, which was kind of like this always on and so on and so forth. When I came to California and I, you know, I used to go to my friend's house on the weekend and you know, the normal conversation around the water cooler was always around entrepreneur X company Y and the guy do great. So like the fact that, and that's really, I think something that is amazing, Scott, about America, which is the can do is in the water, right? And it is I think for the individual that really wants to be that person, for them to grab that. So when I was here in the early 90s, kind of, you know, doing my first entrepreneurial job, and those were the conversations on the water cooler or with my friends on the weekend, I was like, I look back at my own skill set. I'm like, I can do this. I can be that guy, right, that they're talking about in the third person. And that sort of just changed me and made me this got the fire going inside of me, man. Remember, I was kind of in my 20s at the time, right? So this is not somebody that's 17 or 18. So I'm like already through grad school and doing my first job. So I think the long answer for your short question is I think entrepreneurship is something that could be absolutely learned and the fire can get lit at any time in your career. And it just comes down to if that spark happens, you gotta lean into it.
- [10:32]
Scott Clary
How do you know what to lean into? Because you built, I think so you built two companies, so Scopus and Octane. Octane was the $3.2 billion exit. That's massive number.
- [10:43]
Tim Gulari
Right?
- [10:43]
Scott Clary
So obviously you leaned into something that was working. But for an entrepreneur, I think that's the biggest difficulty. One, there's a lot of difficulties when you're an entrepreneur, but one of the biggest difficulties is there's two competing thoughts. Right. So should I keep investing into this? It's always going to take longer than I expect. I know that, you know, maybe it's not going to be at the two or three year mark, but the seven, eight, nine, ten year mark. I'm going to start to see that bell curve, growth curve, hockey stick growth curve, everything up into the right that I was hoping for. Or on the flip side, I'm putting all my time and energy into something that I can't really validate. Product, market fit. I'm not seeing the traction. Maybe I should just, as Kevin O'Leary says, take it out behind the barn and shoot it. So when you're, when you're trying to invest your life and energy into something, how do you validate if it's an idea that you actually want to commit yourself to?
- [11:37]
Tim Gulari
I think the two, two ways to think about it, I'll tell you my journey and not every entrepreneur's journey is that way. I was lucky to be early at Scopus. I was like employee number seven. And this was a company that was in the customer relationship management space. So I call it the granddaddy of salesforce.com right. Like the first OGs in the space. Scopus, Vanta, then clarify. And that was my light mba. So in other words, I joined in sales engineering. I rose up to the ranks in sales engineering which is where you learn all about selling and kind of, you know, what do the customer want and kind of. And remember I was an engineer coming into the job, so I had zero knowledge about sales or you know, you didn't even know what a quota was or what these sales guys do for a living. And then I was lucky that my CEO Oris Hassan and the, you know, my now very close friend Aaron Ahmed who ran Sales gave me an opportunity to move from there to marketing. And so, you know, I call it the live mba because I'm in this company that is growing. I'm getting functional, cross functional training. And that sort of gave me, along with my other comment earlier about just being very naturally inclined because of those conversations that I got to do something entrepreneurial. It gave me the skillset and the confidence that, hey, I can do this right? So the point I'm trying to make is that if you can set yourself off as a young, young person in a company where you can learn those skills on somebody else's dime, that actually sets you up really well that when you're doing your own company, you don't make the mistakes. And the beauty about startups is that, you know, I race cars now for, for, you know, for entertainment and sort of, you know, when Your ass is 2 inches from the ground, you feel every bump, right? And that's different than, you know, being at a larger company like a snowflake or salesforce.com, but you might be just in a single department. So what I tell entrepreneurs or want to be entrepreneurs is get into a well run small company because that's the easiest and the fastest way to get cross functional skills. And I think that's what's going to set you up when you do your own company to really execute and then make the most of it. And the second part of that is that also gives you kind of these filters that says that when you're doing your own company, hey, this is not working. And hey, should I go and shoot this idea behind the barn and try the next thing? It also gives you contacts. Like I was able to hire the handful of first engineers at Oqtane because of my tenure at Scopus. So my co founder, Kira McGhan was now the president of RingCentral, a very successful public company. Came from that because she and I, you know, got to know each other and we said, okay, we're going to do octane together, right? So you get, you get venture capital contacts because I was presenting to the board when I was at Scopus. You get coworker contacts like Kira, you get customer contacts. So first three contracts actually came from customers that had churned from Scopus. And I just went to the same guys and said, hey, I've just hung the shingle, I'm the guy. Will you, you know, we did great business before. Will you give me a chance? Right? So there's all this benefits of working in a really well run startup company before you do your own.
- [15:15]
Scott Clary
So it just, I mean, when you do this, you massively de. Risk building a company. Yeah, because you see it because of all the, the entrepreneurs that come to you and probably pitch to you. But do you feel like there's a, an incorrect shift in the definite. I mean, I don't think it's new, but an incorrect shift in the definition of entrepreneurship where people are like, forgoing any work experience and just trying to build either right out of school to emulate like a Zuckerberg. I want to build. The next thing I'm going to drop at Stanford. I'm going to go build a company or even people that don't want to build a tech company. I feel like social media, it propagates this idea of it's so easy to build, it's so easy to, you know, be an entrepreneur. And, and you see it, you're front line to this. Do you see a lot of people sort of foregoing the delayed gratification and trying to get this instant entrepreneur result and then backfiring on the, on the, on the, on the back of that because they haven't put in the reps and the work?
- [16:19]
Tim Gulari
Yeah. So I think, firstly, look, I think it's, it's super commendable whether you're right out of school and you jump into, you know, solo entrepreneurship because that's the fashionable thing to do and all your friends are doing it, or you go the journey that I was describing, that I went where I worked at another company for five, six years, and then I started my second, you know, my company, which I started. Right. Which was Octane. But in both cases, kudos to you because you're an entrepreneur. Right. So let's start with that. Right. Because it takes a special, special person to, you know, be that. Okay. And there's learning in both, I think, both paths. I do feel that, that on the first path, where you're just kind of launching yourself and, you know, you know, a handful of kids in a dorm or whatever, I think the, the, the probability of success is much, much lower. Right. Because you just don't know what you don't know. And so a lot of these, and we see this with Y Combinator and other incubators, where the team that came through the YC batch, x, x +2, x +3, they come back and that's the real company. So I mean, if you look at the YC sort of alumni book, they talk about Airbnb and they talk about all these high flyers, but there is 98% of these classes actually just train you to be an entrepreneur. But you're learning. That's kind of the Scopus example I was giving you. And then you come back next time around ready for knowing what mistakes you made and, and then so and so forth. So I think to me, if you were planning it out, you know, and you're like a new, you know, grad, and you were trying to like, go, hey, I'm entrepreneurial, I think going down the path where you put yourself in an entrepreneurial school while you're building the idea puts you at the, you know, in a much higher category of success. And even then it's not easy, but at least you break the risk down and you have some skill set to, you know, to push yourself forward and.
- [18:32]
Scott Clary
When you, when you sort of walk through. Because obviously your journey shaped how you approach investing and how you approach entrepreneurs. So your experience, how did it shape your investment thesis? How did it shape what you look for in entrepreneurs?
- [18:47]
Tim Gulari
So I think the first thing is that entrepreneurs that I like are the ones that they have an insight about the future that is not consensus. So, you know, there's this classic kind of, you know, categorization which I'm sure you heard of, which is contrarian, contrarian investing, non consensus investing, and, you know, consensus or beta investing. Right. And contrarian investing, as the name suggests, is where you get the most alpha but the most risk. So this is like you're looking so far ahead and you're taking a complete flyer, right? Yeah. Consensus is where you're just following the market and in the middle is non consensus investing, which is the one that I like, because this is when you're seeing the world through the eyes of the founder. So what I try to do is hang out with these founders that come through us and try to connect the dots. And what is it that this team or this founder is seeing that the rest of the market is not seeing that? I believe it because, remember, we're doing early stage, right? We are trying to be like the first institutional check into these entrepreneurs that one of the real companies in the B2B market, so that's the Sierra Ventures, is ICP. So I looked for that in these founders. And that comes from my own journey as an entrepreneur. Because when I started Oqtane in 96, CRM had happened and there was like Scopus and Siebel Systems and these big companies. But the shift in the market was the Internet was happening and I was confident that the Internet's gonna once again change the customer interaction. Sort of landscape. And that was my insight as an entrepreneur. And that is what, you know, my investors, Greylock and Sigma backed and that's how I built the company. So I look for the same pattern match now when I'm meeting the founders and then my job is to agree with them that this is the road that you need to execute on to de risk that idea such that you can get the first handful of customers and the next handful of phenomenal investors to put fume in the tank.
- [21:11]
Scott Clary
So I even think, oh, sorry, I apologize. No, I was going to say even your journey from operator to investor I think is a little bit interesting. And I would say not common because. Okay, so I have to understand this. You can, you can sort of walk me through this story. I think it's fascinating. So you had a $3.2 billion exit. That was Sierra was the entity that acquired Octane. But then there was no Oqtane was.
- [21:37]
Tim Gulari
Acquired by Epiphany, which me and then I hung out at Epiphany, integrating Octane into Epiphany. But the then CEO and a dear friend of mine, Roger Siboney. And then while I was at Epiphany as one of the officers, I met Peter Bendel, who was the founder of Sierra and one of my good friends from Scopus, Dave Schwab was also a partner at Sierra. That was a connection.
- [22:09]
Scott Clary
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- [24:53]
Tim Gulari
So the slide is interesting. So I obviously knew venture capital because I'd raised money from some of I think the best firms in the valley as an entrepreneur. And so I knew the venture capital game. You know, return for them half a billion dollars each, you know from the opt in experience. So you know at least like a half a billion reasons for each of them to make yellow still be dear friends. And now we co invest together. But then I'd never quite formally thought about becoming a vc. You know I was kind of on my second company and I was like yeah, I'll do a third or a fourth or whatever. And then I happened to spend time With Peter and Dave and Sierra felt like a startup at that time. The firm had been around already for 20 years, but the way they were thinking about and helping early stage founders, that was what my love was. So I spent a few, you know, a little bit of time on with the. On board meetings with Peter and Dave, and that's when I pulled the fritter and joined Sierra in 2002.
- [25:58]
Scott Clary
Okay, that makes a lot more sense. I was wondering, I was like, yeah, I was like, I don't think Sierra had the capital to make that kind of acquisition. But then I was thinking it was some sort of private equity place. Okay, so Octane was acquired by PubCo, and then this was just relationships that led you into Sierra. Okay, how has Sierra, how has Sierra changed? I mean, why? When? Over time. What was their thesis and what was their strategy when you first started talking to Peter, what has changed over time? What's evolved?
- [26:31]
Tim Gulari
Yeah, I think Sierra is. Is a phenomenal brand very well, you know, has served like some of the largest companies. Stratacom, which became the core of Cisco, was our investment. You look at the beginnings of erp, so Intuit was one of a signature investment that actually Peter Vendel made himself and so on and so forth. So lots and lots of history before I joined the firm. But in 2001, 2002, you recall that this was like right after the craziness of the Internet wave and the crash of the market in the early 2000s. And so what the firm had become, the fund had become very large. And we were doing early stage and late stage. And it became clear when you roll the clock forward kind of to 2010, 2011, that that strategy was not something that I was excited by as one of the general partners and my two other partners, Mark Fernandez and Ben Yu, we wanted to do early stage and we felt that sort of a split strategy would serve neither masters. Right. You're not doing a good job in early stage investing or mid stage investing. So that's kind of when we discussed with the rest of the partnership and took the thumb down the direction of early stage investing. So in 2012, Scott, I would say was the birth of what I jokingly call Sierra 2.0. So we reinvented ourselves in the sense that we got clarity on mission. Right. The brand had been around. You know, the firm now is over 40 years in business investing, our 13th fund. So one of the iconic, your names and B2B tech investing. And really lucky to be given that pedestal by our limited partners and entrepreneurs that choose to work with us. But what really made it clear and fun and started in 2012 when we effectively took over the management of the entire firm because I was an individual partner before then and then 2012 on onwards running the firm along with the partners market. Ben is now we had a very, very clear North Star which is you want to be the first institutional check in first or second sometimes because now these are precedes and all kinds of, you know, fun stuff happens before we find a great investment and then you.
- [29:15]
Scott Clary
Fun, fun stuff's in. In air quotes.
- [29:18]
Tim Gulari
I agree. You know, friends and family rounds and pre, pre see all kinds of stuff. Right. But you know, sort of this come early, stay late mentality. Right. That nothing great gets built overnight. Okay. And you have to have the courage as an entrepreneur to, to realize that and lean into that commitment and then we will be your thought partners and capital partners to kind of take you through that journey. And I think what really helps is that, you know, I've personally been on the road multiple times, taken several companies public. You know, we've kind of have all the arrows in our back. So it's like, hey, I really suggest you don't walk down that alley because it's going to hurt. Right. Because we've been there. And I think it's that authenticity of brand and love for entrepreneurs and everything they go through and deep, deep respect is what I think. You know, Sierra has come to become. And then obviously we do a lot of other stuff. You know, we have old CIO advisory board and all kinds of infrastructure to help these guys get the first 10, 15, 20 customers. But that's a little, I think a backstory.
- [30:26]
Scott Clary
Yeah, I know that makes I love it. And I think that again, if you've, if you've played this game before and you've built companies multiple times, then this may not be a surprise. But for a first time founder, maybe just describe the importance of. I love this philosophy. Come early, stay late. I think that's, I think that's an incredible philosophy and I, and I want to sort of reinforce how important that is as a first time founder, what that's going to mean to you and your journey and just having somebody who's really in it for the long haul. So maybe talk about the importance of that. But also I think it is important without naming names because that's not cool. But talk about some of the traps that founders can fall into when they work with other types of firms.
- [31:11]
Tim Gulari
Yeah, I think, look, I think it's ultimately founders have to be very thoughtful about the kind of journey they're going to embark on. Right. So are you sprinting and you're, you're building muscle memory to be a sprinter or a marathon runner. Right? Because you know, the way you train, the way you eat, your regimen is very different. Right. So if you're trying to be Instagram and kind of trying to get to a billion dollar outcome and you get bought by Meta, that's a consumer company, different looking. That's like what I think the industry starts to call blitzscaling, which is like just pour a bunch of gas and good stuff happens. We don't believe in that philosophy of incinerating cash. We like to build solid foundations so that you can build the tallest building in downtown. Right. Like it just takes, you know, very, very thoughtful, methodical, execution, understanding also that along the way there'll be a lot of like discovery and your decisions that have to be made. That might be painful, you know, for the entrepreneur because you letting people go or you're, you know, moving strategies. But again, somebody that has been that done, that has a steady hand on the pill and you know, really work entrepreneur hours, I mean, you should talk to some of the entrepreneurs that, that I'm involved with. Mark, my partner, Ben Shashank, et cetera. I mean last night I was on a phone call till like 10:30, right, with some guy and we're texting, right? And the guy like, hey Tim, you're awake. I just finished dinner. I'm watching, you know, the game yesterday, the playoffs and bang, you know, he just calls me. We have a quick like half an hour conversation and it doesn't feel like work to me because honestly I don't think I've ever worked since 2001. Honestly, Scott, like, and I, you know, don't tell my partner this, I shouldn't get paid a dollar for doing this, right? I'm having, I have so much fun because, you know, I love these entrepreneurs. I love what they're building and we're invested in it. Not just writing the check is the easy part. Can you give them the time? That's the hard part. So I'll answer your question, which is when you're choosing a VC partner, don't worry about the cash as much as worry about the time. Are they going to give you the time and really be there? Be a thought partner as you're navigating these halls and alleys I was talking about before and I think if they cannot give you the time, which is what happens when you're multi stage and multi Billion dollar fund. Because look, you cannot possibly have time because you have 300 people in your organization. You have $7 billion to invest. You're writing like $150 million checks a piece. That's a different beast, right? And those gps also make great money for the investors. But that is not the game that we play. And I don't think that's a game that early serial entrepreneurs should be looking to play. So I have a pretty deeply ingrained view on what a great venture partner is at this stage, early stage of a company which is giving you the gift of time. And you can only do that if you're making these concentrated bets, right? Like I write like one check, maybe one and a half check a year, you know, and so do my partners. So we're not spray and pray. We're not like doing, you know, 70 companies. It's a very conviction based investment strategy. And you know, I think that's paying us very well. And LPs and funds are doing great because of that.
- [35:07]
Scott Clary
I, no, I think it's smart and I think it's a healthier strategy for the entrepreneur because the Spray and pray blitz scaling. Oh, it's okay. If nine companies fail, at least one will be a unicorn. I think these are very toxic ideas and I don't love these ideas. And sometimes entrepreneurs just see money and they get excited and they, they jump at the money and they don't realize that like, listen, your, your life is not going to be as great as you think it is just because you take, take some money from an investor. So yeah, I think it's important. I, I, I love that you're, you're so focused and you're so careful and thoughtful with your checks because that means that. And another idea, money is relatively cheap, but time is very expensive, very expensive. So to get time from a managing partner is. Yeah, I don't think that happens that often. Yep, I, I really don't. I mean, what your risk is that you make the wrong bets. So maybe just talk about how you make sure that, that one one and a half checks that you write per year is not on the, is not betting on the wrong company or the wrong person.
- [36:20]
Tim Gulari
I think that's a, that's a great, great question. And you know, the interesting thing about venture is, Scott, that, and the reason I love this, this, you know, job that I do is that you cannot rest on your laurels because the market and the technology trends keep changing. So you always have to keep repotting yourself. So 20 years doing this, I can still tell you that I'm still learning and I still have that, you know, that, that learner's mindset personally, you know, because it's just like. And I learned a lot from entrepreneurs that teach me a lot. And I'm constantly looking for that, right? Constantly spending time. Like today I have lunch with the chief digital officer of gsk. You know, we're going to spend an hour together and I mean, she sits on top of a massive budget. So, you know, both on the industry side, entrepreneur side, and then senior execs. Right? So we're constantly learning. I think for me, what I think is super important is that these learnings are the stuff that you transfer over to these entrepreneurs so that the transfer learning on the osmosis is happening and they're just figuring this out and not again going in wrong directions or making the most efficient use of the capital that you've given them. Right. And so we do six optimizations in the seed through series A journey. And the six optimizations are, there's product marketing or, you know, product positioning optimization, there's team optimization. So how do you structure your team? There is company positioning optimization. So the whole series of exercises we take the entrepreneur through, like, okay, what is the category? What should you really call it? Right. There's a financial model optimization, there's a whole series of excises there. There's a cap table optimization which is like, okay, cap table is very much like cash. There's only so much of it to go around. So there's a whole notion of, okay, how should we think through C to A to B to. Cuz ultimately we're on the same comp plan as the founders. We're working for equity and equity value. Right. And the final is, you know, funding a fundraising optimization. So these are the sub pillars, if you may, of building a great foundation of a startup company. And that's what we spend time on. And I think that's what makes great companies happen. The mistakes are when and we make it, and I make them personally as well. Where. And most of these had to do with the individual CEO that we took a bet on and that bet ended up being wrong. So the read of the CEO or the read on the CEO or on the market. Right. Was not like on the nose. And I'll give you a couple of examples. So in one instance, it was a seed check. It was a company that was based in the Rockies and it was a very, very aggressive and a very fundamentally disruptive idea. So we seeded this company along with another Small seed fund. I think they raised maybe three and a half million bucks or so. And then the year into it, the CEO was not seeing the North Star be the North Star. So the market had shifted quickly. OpenAI had done something different than what expected them to do. And suddenly that market idea disappeared. And the CEO just called me one day and said, hey, I'm going to do something else. Right? So that's an example of two things going wrong in that opportunity. One is the CEO's resolve to work through or not. Right. I, I didn't read it correctly. I thought that, that, that particular gentleman individual would actually go through that wall, but he chose not to. And the second is we didn't expect the market to shift. So no harm, no foul. You know, I'm still, you know, very friendly with that CEO. But that's what seed bets are all about. You know, you, you, you make the best sort of bet based on the information you have at hand at that particular point. And, you know, you truly understand what you have. Once you're six, nine months into the.
- [40:56]
Scott Clary
Journey with the entrepreneur in a situation like that, is there something that you could do to, or that you try and do to help the founder, CEO align on the same vision, like realign? Because from every person that I've spoken to who does venture investing, the, the individual is the most important component. Like, yes, the market can shift, but the individual is the X factor. Like if that person goes rogue, you're done. So what, what are, what are the as. Let's talk to investors in the audience. Say they put money into an early stage company. What can you do in that case? Is there, is there strategy? Is there a tactic or is that write off?
- [41:44]
Tim Gulari
Yeah, I think so. The first thing is that do as much work as you possibly can before you write the check. And I really mean this with all the, this is why I'm not a fan of these party rounds that happen over the weekend and Everybody's writing a 300k check and then nobody shows up for work. Right. Because there's no ownership to the project. Right. The founders raised 4 million bucks, but everybody's put in 200k, like, okay. And then there's no, you know, there's no, nobody to challenge your ideas or give you new ones. And it's a very lonely place to be. So if I was advising, you know, entrepreneurs, I would say don't do that. Right. Investors, which is the question you asked. I think I now have a much more rigorous process on understanding the individual behind the CEO. Right. Like what is this person all about and doing like, you know, blind references and other calls. Now one of the benefits we have as a 40 year plus venture capital firm is we have, we're one call away for almost any entrepreneur to find out like, you know, what are they all about? Because you know, we've got such a massive network, right? So unless you're a ufo, you know, one of these kids from college that doesn't have a history in the Valley. If you've done five, seven, ten years of work in the Valley, we know one person that you know will give you. Yeah, so I do a lot of work in advance. I also spend a lot of time with them, sort of off cycle, taking them out for dinner, go for a walk before we write the check. This is really to unpack the person behind the person. But I think having said all that, things that still go wrong because people are people. And so the answer to that is for the listeners that are investors is surround them with a highly skilled set of either co founders or advisors early on. And I think because CEOs tend to learn by osmosis, the best of them, they have a learning mindset. And a great example of this is one of my favorite CEOs, Maya Din Reddy, who's running now a very, very large company investor in this company based in Philly. It's a company called Phenom in the HR tech space and just a rocket ship company profitable while all the other competitors have burned and Scott incinerated hundreds of billion dollars of cash here in the Valley. This guy's kind of, you know, raised less money than the ARR that he's putting onto, you know, on his top line every year right now. Just a phenomenal company. And the big, big thing that I respect about my is that he surrounded himself with. He's always seeking out that next great idea from the next great person, right? So the job of the early stage entrepreneur is given capital, doing all your work before you write the check as much as you can, but still can, things can still go wrong. And then surrounding the CEO with what I'd call experts or people that can really give them additional ideas once you've identified what their soft spot might be. So one of early stage CEOs happens to be this phenomenal founder from PayPal. Technical guy, had to learn go to market on the job, right? So I've like inserted like this guy whose company I've invested in that you know, worked at a very, very great company on the GTM side called AppDynamics. And that person is now advising Suresh, who's the CEO in question, that this company I've done called Saday on gtm. So again, that's a great sort of a fit and he's learning a lot from them. And I think that brings down the risk of these founders going off the trip.
- [45:57]
Scott Clary
I think that's very wise. I also think that it's sometimes uncomfortable for a first time founder to ask for help and understanding that there's a mental block there for them to put, you know, put them in that, a little bit of a position of I, I'm, I'm sort of saying I don't know what I don't know and, and please, like I want the advice. But I think there's an ego involved in that too, that a lot of people have a tough time asking for help. So if you're putting those people around them, you're just, it's just a very great environment that's going to allow that person to thrive.
- [46:33]
Tim Gulari
The other thing, you remind me of something, Scott, when you said that. The other thing I've kind of noticed is that these founders talk to other peers and get quote, unquote advice and lock into that advice, which might be different, maybe by a few degrees, sometimes completely opposite to the way I would advise them on that particular point. So I've been through thinking about that because, you know, One of my CEOs does a lot of this where he'll go and talk to another CEO who's 28 and try to get advice on fundraising or timing of fundraising and so on, so forth. And I'm like, that is not that guy. Personal gal is not giving you the right advice. Right. So the point here is not that don't talk to your peers, you should but filter what you're getting based on the experience that somebody has. Right. Because it's more likely, I'm not saying I'm always right. It's more likely that somebody that's gone down a path that has a perspective and does this professionally, it probably give you better advice than your buddy you're having a beer with. Right? Yeah.
- [47:49]
Scott Clary
And sometimes I've actually found this a lot. And I think that it's also very damaging. So if somebody achieves some early success and they haven't been in the game long enough to understand that their early success is not the, the way that they achieve their early success is not the only way to achieve success. They become almost like there's like a, like a religious conviction about how they achieve success. And that's the only way to do it. And that's the only advice they give. And they speak with such conviction and such charisma that you know, the receiving. The recipient of that advice starts to believe that yeah, that must be the only way to do it or that must be the only way to operate through this specific. And they're only like, you know, they're 25, 26 and they're giving, they're giving this advice that served them well for the first, you know, four years of their life. But they don't realize that multiple things can be true at the same time and that what worked in one industry or one instance, it doesn't always carry over. And this is bias towards this, you know, their, their short lived experience. And I think that's also damaging and that you probably get that from peers.
- [48:53]
Tim Gulari
The balancing comment is right. This is not a age thing or an experience thing. Right. Because I think that I met 22 year old that are, that are very, very insightful and they have a different set of experiences. So I think the point I think we're both trying to make is as a, as a first time founder, understand the source, put a filter on top of it, okay. Figure out, you know, based on a lot of life is all about having a gut instincts, right. So when you've had enough reps, you just know, right. And so they need to get enough reps. And you know, if you're, if you're taking feedback from founders, go talk to 10, not one. If you're trying to take, get feedback on a particular point from like tenured VCs or whatever top to fight not one. Right. And then you balance it and you'll get the right and then apply our own intuition. So this is kind of having one conversation over a cocktail doesn't make a strategy.
- [49:50]
Unknown
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- [52:03]
Scott Clary
You know you mentioned six six pillars correct that you that you work through to help the entrepreneur optimize their business. First time founders, which pillar do they have the most trouble with? What's the the biggest issue they have?
- [52:16]
Tim Gulari
I think first time founders have the biggest challenges with positioning. Like what's the how do you position the company? And they don't understand the importance of positioning on a relative basis because positioning is needed not for, you know, TechCrunch or whatever, but it's needed to to clearly deliver your 30 second pitch or 2 minute pitch when you're talking to a prospect. Right. That's why positioning and positioning is a relative exercise. It's not an absolute exercise. Right. So we could chat about that maybe later. So I think that's one thing that they struggle with a lot and the other obviously is the product, the GTM side. Right. Because a typical archetype Scott Farrar founders is that they're technical, deeply technical, come from a deeply technical background, don't quite know gtm and that's the muscle that they have to learn. The rest of the stuff is, I think, relatively easy, you know, like finance and cap table and so on and so forth. But those two are the ones that they are the least sort of knowledgeable about and have learned. And the next thing I'd say is once they've been in seat for a while, the successful ones figure out how to build teams. The CEOs that sort of power through the learning curve and continue to grow are the ones that actually are like, have this amazing instinct to find the best position players in the market for what they're looking for before becoming necessary. So before you need that amazing BPO marketing, you've already been talking to and had dinners with a bunch of people that point you towards that they're always six to nine months ahead. Right. And again, building the team, I guess is the point, but putting in the work to build a great team is the ones that, you know, great entrepreneurs do. So I'd say those two and then the team building being sort of the, the next one out of the, out of the six.
- [54:32]
Scott Clary
You mentioned a nuance as to how we look at positioning.
- [54:36]
Tim Gulari
Y.
- [54:36]
Scott Clary
Can you go deeper on that?
- [54:38]
Tim Gulari
Yeah. So I think the, the positioning exercise is. And you know, I'm a big fan and I'm sure you've obviously read and heard Simon Sinek's, you know, the Onions, right, The three circles. I think for me, what I try to educate and the discussion and the whiteboarding that I do with these founders is like, how do you relatively position your product or your offering? And what I mean by that is in technology everything moves in waves, right? And so if you're innovating now in wave number three, you have to have a narrative and a story that talks about wave one and wave two and this notion of why this, why now? Right? That's a question. You gotta be able to answer that why does this company deserve to exist now? And once you answer that, and that answer to that is based in a, in a trend that's going to happen whether that company existed or not. You know what I mean? So for instance, I have a great company that is doing some incredible early stage work in E Commerce search that came out of MIT and they've invented something called Customer GPT. So it's basically a transformer that can detect customer behavior automatically without looking at log files and all that stuff. It just what every other technology company before that is based on. So there, why this, why now is this Customer GPT which is Anchored in generative AI, which is happening now. Right. So when that CEO talks to the market, says, hey, this could not have been done before 2022, because now is when this technology got built. So we're like part of that generation. Right. But to be able to articulate that becomes important. And then the second thing is, okay, relative to what? Which is the question, the point I was making, which is like, okay, if indeed you're innovating on that technical curve, relative to which companies are you better and how. So that's a relative positioning that I think entrepreneurs sometimes struggle with and we help them unpack that in a way that the narrative and the story and the two minute pitch to the chief digital officer of gsk, who I'm going to go see today, if they were sitting in the room, you got two minutes to tell her what your company does. And it just needs to be very crisp. So it needs to come out anchored in a tech trend. Why this? Why now? And the next thing you have to talk about is relative to the other options you have, why would this be better? And then the third is, hey, we can deliver this. So it's that narrative which is super critical.
- [57:24]
Scott Clary
There's two thoughts on that, actually. I'll go into the first idea quickly, but is it always required? I would say for Sierra, obviously it seems to be a requirement, but to have entrepreneurial success, to find true product market fit, to have some sort of hyperscale opportunity.
- [57:46]
Tim Gulari
Yeah.
- [57:47]
Scott Clary
Is it always required to find some sort of tech trend or wave to piggyback off of? Or have you seen entrepreneurs that truly find novel ideas that have not been explored but are not sort of time bound?
- [58:00]
Tim Gulari
I think that's a great question. I think there's plenty of examples where the innovation was not anchored in a tech breakthrough, but was anchored in a distribution breakthrough. Right. For instance, I'll give you a great example. One of my first investments was a company called sourcefire, which was in the information security space. So this category called IPS Intrusion prevention system. So the notion that you put these devices on your network and if there's any intrusion happening on the network, they're able to detect it and audit. Right. So yeah, we wrote the first check into this company, I think five pre, raising $3 million or something, and it took us a decade, but took the company public and Cisco Systems bottomed for 2.7 billion. Now, that company and Marty Roche, who was the founder, was not based on a technical innovation or a discontinuity in the market. Right. Check point was already in the market, selling their product and a whole bunch of other people. What Marty did, which was masterful, was that he, it was an open source company and he built an open source based piece of software called Snort and Snort just got insane adoption in the market. Right. And because of the distribution. When we met him first, when my partner Mark Fernandez and I went and met him, he was kind of building appliances for Honeywell and for all these enterprise companies out of his garage. And the reason was that they loved the open source product so much and they were saying, hey, can you put this in an appliance and give us a SLA and we'll buy it. Here's 150k, here's 100k, intel, et cetera, et cetera. So that was a great example of a distribution advantage that he was able to sort of ride the wave on and that became one of the most successful companies. I still remember the board meeting right before we went public. There were only three deals, Scott, in that board meeting that were above 500k. Every other deal was like sub 100k, give or take. Right. Which means that just the power of the distribution. Right. And the fact that you had these 50k, 100k deals that are being bought all over the world is what they exploited and became a great company.
- [60:27]
Scott Clary
Do you think that there is a playbook for understanding potential distribution that has not been discovered yet, something that you would recommend other entrepreneurs look for that you saw with Marty?
- [60:38]
Tim Gulari
Yeah, so I'm a big fan of open source. Obviously, you know, we made a ton of money using open source as a distribution channel and a source of competitive advantage. So I have a very successful company based on New York called Astronomer, which is building data pipelining software. So data orchestration. How do you connect a snowflake, you know, to some other, you know, system that you're trying to move data to databricks or something else, and that's based on open source product company called Airflow. So open source is very well understood and that's something that is, you know, certainly it's going to continue to kind of, I think, pay dividends. In fact, Dave McJanet, who's the CEO of HashiCorp, which got sold to IBM recently, and I were at a football game. He's a good friend of mine and he said in one of my interviews, I did fert with him that in his opinion there will not be an infrastructure software company with consequence being built in the future that is not open source. So he's like that black and white on that point. Right. And there's some truth to that because if you look at the cost of distribution as the Companies get to 500 million, ARR. You take 40% of 500 mil, right. You know, that's a lot of money. Right. And then double like what you're spending in sales and marketing. So if you can shave off like 15, 20 points on that, that just drops to the bottom line. So that's where distribution becomes important. But the other angles are, I think consumer and enterprise are becoming, you know, coming closer. More and more customers are discovering what enterprise product does or doesn't do sort of themselves on top of the funnel. So a lot of the techniques that, you know, we've used traditionally in consumer marketing, which is drive before you buy or paywalling or information, you plaster information. And people come through these social channels like LinkedIn happens to be a very effective channel for a lot of my startup companies. A lot of them actually use TikTok as well. We'll see what happens with that, which, what's going on with the controversy there and the decision on the Supreme Court. But I think consumer coming closer with enterprise and the techniques that they use in consumer marketing are going to bleed into what I'd call traditional selling in the enterprise. And I think that's where there's lots of innovation to be unpacked, lots of opportunity.
- [63:20]
Scott Clary
The second sort of thought or question I had about when things hit this massive growth, when a company has this massive growth curve and everything's working out, obviously that's every entrepreneur's dream. But I do know that that's also when a lot of things can break. Yeah. So when a company is, is scaling and you have product market fit, obviously this is great. But what should founders or entrepreneurs look for or pay attention to so they don't, so it doesn't blow up in their face?
- [63:49]
Tim Gulari
Yeah, yeah, that's a, that's a great, great question. And you know, I'm lucky enough to been board members in these companies that have gone from like 50 to 150 in. And that's exactly when the kind of, that, that, that, that, that stress starts to shape the airplane. Right. And you don't want to see the rivets flying off right midair. Right. So I think the most common issue that occurs is the two things that occur. One could be the cost of sales and distribution. Right. So the point being that, let's assume for a second you have a very deep balance sheet. You've raised like 2,300 million dollars, so you've got unlimited fuel you can hire 30 sales guys or you can hire 80 sales guys or gals. I think what traditionally happens is or typically happens, and something that farmers need to watch out for is what is the cost of every incremental ARR dollar that you get back based on what you're putting into sales and marketing. And there are lots and lots of metrics to measure this. There's magic numbers, and then there's kind of the overall efficiency of the P and L, which is called the burn number or burn ratio. So I think that's culprit number one, which is the inefficiency of the selling unit. Whether that happens in whether it's A's or account exec set, right? Like, what production are you getting per account exec? Because there's many, many ways to hide the inefficiency in that, in that group, right? Because you could be losing reps, you're not training them well. I mean, there's all this bleeding that happens. So your top line is growing, but you know, it's coming at a incremental expense. And the problem is if you don't fix it when you're doing 50, it's going to be so expensive when you're doing 150 that it's just going to. The company's going to just kind of keel over or the growth rates are going to come down. So the efficiency of the sales and marketing engine at 50 million ARR is the most important thing to focus on and something that trips up entrepreneurs the most. That's number one. And number two is tech trends like what's happened with ChatGPT and LLM, where a technological wave comes at you so fast and you don't sort of pivot the company fast enough. And I was hearing a podcast from one of my favorite CEOs, you know, Marc Benioff, just on the Saturday. And Benioff talks about the fact where I think he was talking to Steve Jobs and, you know, Jobs sort of pivoted the whole company on the iPhone and the iPad, right? Like, he just went boom in one direction. And in that particular podcast, he calls it the Steve Jobs moment, right? Where you just like have so much conviction as a CEO. Just you say, hey, we were going here, bang, we're just going to go there. And he himself talks about how he's done that at Salesforce with this agent force change in architecture. And I what I didn't know when I was, when I heard the podcast is he actually did made that call two weeks before Dreamforce. Okay. Which Is like crazy to me, right? Two weeks before Dreamforce, he went in front of probably his marketing at PM and all the people, hey, everything is agent force now, okay? Go rip up those PPTs, build them again. You know, like signage, all that stuff, right?
- [67:33]
Scott Clary
Wild.
- [67:34]
Tim Gulari
And I'm sitting here going, okay, but.
- [67:36]
Scott Clary
So much conviction, though.
- [67:37]
Tim Gulari
So much good days, and we're taking that hill. So I think that is culprit number two, which is what I'll call the slow boil and the, and the, and the frog and the, and the slow boiling water, right? Where entrepreneurs just, they know what's happening, but don't have the confidence and the cojones to say, hey, let's burn the bridges behind us. This is where we are going. And there's a lesson to be learned about that from Benioff and other big.
- [68:05]
Scott Clary
Jobs have you found in your life as an entrepreneur, as an investor and some of the entrepreneurs you've invested in. There is a decision making framework that.
- [68:16]
Tim Gulari
Works very well for which of these.
- [68:20]
Scott Clary
So, no, for making such a drastic, high conviction decision. What is. I guess the question is like, what's the signal? That's. I mean, maybe it's just intuitive, maybe it's an unfair question, but somebody's listening to this being like, I don't know if I should, if I should be pivoting or not. Like, it just seems like overnight all my work could blow up if I make the wrong decision.
- [68:42]
Tim Gulari
No, I think that's right. That's a great question. I think there's, there's, there's. What my companies do is we first recognize this rapid shift at the board just in a board meeting setting. And then we do an internal exercise which is, can we do a little tiger team, like take three people in engineering and let's prove that the tech actually dramatically works because the customer is looking for the same outcome. They just want it better, right? Cheaper, faster. So there's an internal exercise that we do, and the other exercise is an external exercise where we'll go and talk to our top 10 customers and run this idea past them almost like they were as part of the company. And with those two signals, you have enough data, internal and external, to make the call. And the call might be, hey, let's wait for six months, but that work has to be done. And unfortunately, there's no framework like a MBA sort of framework that you were talking about, which can be applied to this. Right. It just has to be this inside look, outside look, quick call. And the call could be go or wait or we'll wait for six months and we'll readdress this. And you also need to look at what competition is doing because competition is not just sitting around. And that's sort of the third axis that might have you move faster or sooner than you initially planned.
- [70:11]
Scott Clary
I think that's very, very smart, very wise. And I think that also just a caveat, having these customer focus groups and speaking to your customers at any stage, even if it's not a major pivot decision, is probably one of the best practices you can do regardless.
- [70:26]
Tim Gulari
Absolutely. I think any CEO that's not spending, you know, close to 50% of the time in front of customers or at some customer facing activity, once you've kind of got the meat and potatoes going in your company, which comes down to that third pillar I talked about, which is your team. So I call it, Scott, the no pass team. The no look pass team. Right. Like, and again, we're in playoff season. Right. So you know, like these quarterbacks that you know are looking here, but the throw there. Yeah. And the ball gets caught. So once you built the no pass team, no look pass team and you're confident that the lights are going to stay on and things are optimal back at the shop, your job as CEO is to be in front of the customers because that's the best signal on where to take the company, where the competition is going and obviously getting your numbers.
- [71:21]
Scott Clary
Exactly.
- [71:22]
Tim Gulari
I used to do that. Yeah, I have no doubt.
- [71:24]
Scott Clary
Yeah. No, I think that's, I think that's such a missed opportunity for founders. One of my favorite stories, I have a friend, Aaron Spivak, and he sold a company, Hush Blankets, for I think 50 million to sleep country Canada. He's a Canadian, we're both Canadians. And he would jump on customer calls and ask them after they purchase and just ask them. Obviously not an enterprise B2B, a consumer product, but still same concept. He'd jump on calls and he'd ask them if they like to purchase, what he could do better. And obviously he got massive feedback. And he'd be doing this up until the day when he actually sold, he'd jump on say 10 customer calls a week. And I thought it was a great idea. And he also noticed outside of the fact that he built rapport, he got, you know, he got this great data from his customers as to what he was doing right and wrong. He also noticed that the, the lifetime value of the customer increased dramatically because they felt this personal connection with the CEO. So usually blankets are like a one time purchase. He noticed after he Jumped on a call with them, on a zoom with them, they'd be buying blankets for all their friends and their family. So like the LTV of the customer. So it's just small things, but it makes a huge difference. It really makes a huge difference. Last idea that I just want to sort of just touch on. Obviously this is something that a first time founder will eventually have to think about be the exit. So obviously you can private equity, you can go to strategic, you can ipo. Tell me just some wisdom or some insight around what the founder should be thinking about, when they should be thinking about it, should they think about it when they raise their precis, should they think about it much later on. What do you recommend founders ideate around exit?
- [73:02]
Tim Gulari
Yeah, I think the way to approach this question is to always remember that the best companies get bought and not sold. That's sort of the first point and that is true for actually even going public because the public investor is also buying, right? And they have an opportunity. If you're Putnam and you're trying to deploy $100 million in like tech, you have options, right? Should I put in Power auto networks or should I put it in Zscaler or like whatever, right? So you have to. The best companies are bought, they're not sold. That's point number one. Second is that sort of mass matters. So in other words, your outcome would be disproportionately higher if you're at a higher ARR. Number of customers, number of blankets, whatever the case might be, right? So you have to kind of be heads down till you get to some mark. And in my opinion, you know, and certainly the work that I do with B2B, that's maybe you become a serious company when you're like 25 to 30 in arrangement. Before that you're in quote unquote, the valley of death where a little sneeze from here and competitive move from there and bang, you're over. Right? So everything else before that is an experiment. Now given that framing, I think that as an entrepreneur you're always looking at technology trends, right? Like is the wave going to come to you to kind of keep rising? The wave that I'm riding, okay, what is competition doing? These are the little guys that are other startups relative to you and what are the big guys doing? Right? Constantly being six, eight months ahead. What is Cisco doing? What's Datadog doing? If you happen to be in that particular space and then realizing that M and A and opportunities to sell. It's like I give this example to my CEOs, it's like in the solar system, it's like celestial objects that are moving in different orbits. And what happens is so you're here spinning away as a small company and here's IBM on its big swing and if they get close to you and my buddy Rob Thomas who runs all a product and all GTM for IBM gets interested in you and he wants to pick you up for 300 mil or 400 miles, that likely is to that, that is likely to be in a very, very short window of time because when IBM swings past the apex they have other priorities and other things. So you have a short window of time to hit that bid or hit that call. And that's what happened with me. So you know, when, when Octane got purchased for 3.2 billion, if I had not hit that window and I was very lucky and got good, good advice and obviously right place, right time, but the market crashed right like you know, six months after that. So if I had not hit that window, it would have been a very different story. Now obviously that is not, it's not true for every single company. Some companies are running so well and so fast that they might have other options. But I think that's again in like single digit sort of probability. And ultimately I think if the market is big enough and I think you have a CEO that's got juice and performances happening like this company Phenom, I think then the world. Sure, because if you ask Mahe, he's just going to, he's on a mission to build a multibillion dollar company and you know, and we're very supportive of that. And because he's producing the results, the competition is falling off and the market is getting just even more interesting. So but you also always have to have a constantly sort of aware mindset on what's happening around and then you know, craft your exit based on that.
- [77:03]
Scott Clary
What would be, I mean we've gone through almost the full life cycle of a, of a, of an entrepreneur. What would be a question that I didn't ask you that I should have or maybe some last words of wisdom or insight or an idea that's even like floating around your head right now that you're dealing with.
- [77:19]
Tim Gulari
I think the thing that I always am thinking of is again I do early stage work and I'm obsessed with this personally. I just want to be associated with the best entrepreneur building the most world building company. So I'm like constant look out for that. When my wife's like what the hell are you reading at 11:30 at night when I get the tap on my head under the blanket or I wake up in the morning at 5:30 or whatever. I think I've been obsessed with this idea of the 100x multiple and first check which is like as a early stage investor you write a check into an entrepreneur and that check 100x's right because the entrepreneur has produced tremendous value and run and that's a combination of the idea, the entrepreneur and the very few companies have been able to achieve that for a seed stage investor. So I'm just, it's not a direct answer to your question on like a new idea I'm thinking about but I'm thinking about the framework or what are the commonalities between those projects that hit that 100x mark and you know, like just also in a way for us at Sierra to be able to find more of those.
- [78:41]
Scott Clary
And that's what you found? Sorry, I was going to say have you found, have you found commonalities?
- [78:48]
Tim Gulari
We have, we have, we're doing a lot of back testing. We have so much of data now. And also looking at external markets, I think one thing is this founder that sees the future before the rest of the world sees it, that just gives them escape velocity before the rest of the market wakes up and the other is really a trend that is not obvious today but is going to be the big wave that's going to break. So this is like the uber example. The 100x thing is something that my friend Mike Naples talks a lot about also at Floodgate. He's also an early stage investor I respect a lot. But the prototypical, what's the archetype of that perfect founder and perfect idea to get you that 100x because I think if that happens the company is going to be insanely successful. So we're trying to constantly evolve a playbook and I think Scott, that's what makes my job as a multi state investor working on behalf of my LPs that are kind enough to give us their confidence and money super exciting because there is no ceiling time I'm here, I'll be talking about the 150X. Hopefully you know, it's like you can do better. Come on. There's no, as I said, there's no A grade in venture capital.
- [80:09]
Scott Clary
Exactly. It's listen, the space you play.
- [80:12]
Tim Gulari
A minus.
- [80:14]
Scott Clary
No, I was going to say the space that you play in is so much fun. It's so much fun because you work with some of the best, most innovative people in the world, they have the best ideas, most innovative ideas. You see the future before it happens, which is incredible, absolutely incredible.
- [80:30]
Tim Gulari
But just to correct that, Scott, we don't, the entrepreneurs do. And what our job is, what our job is to look through the eyes of the entrepreneur and see the art of the possible. So the reason that you know, so we have these startup idea entrepreneurs come and pitch us on right this room right behind me and we have this discussion and oh my God, the light where this could go wrong. I'm like, okay, this is all great, but tell me what could go right, right? That produces a massive company. Let's talk about that. That's the discussion. What's happening. And then like trying to figure out whether this entrepreneur, this team, is the one that delivers that. Right? And to me that's the exciting. It's like you have to be glass half full. And obviously you manage risk at the fund level. You don't manage risk at the individual company level this early.
- [81:18]
Scott Clary
If you want to connect with some listeners, if they're interested about how to work with Sierra, who do you serve and where should they reach you?
- [81:27]
Tim Gulari
So if you're building, you know, thoughtfully building a company in the B2B space globally. So I don't care whether you're in the US or, you know, you're in Europe or where have you, because we invest all over the world and you're looking for, you know, thoughtful, stable partner and firm and does not just mean you get the entire Sierra family and the 80 CIOs that we have on our advisory board and the power of that. Then you should reach out to me. And the easiest way to get to me is just write me an email. I'm pretty. I have an SLA of responding in 24 hours, so. And it's tim@sierra ventures.com.
- [82:11]
Scott Clary
That'S super easy. Okay, I love it. Last question. I always like to finish up with. So this has obviously been a very, a very business heavy podcast, which is incredible. But the last question ties back to a little bit more of it could be personal, professional growth and development. Because the question is really simple. Out of all of your, you know, your experience or success, if you can take all the lessons and they can be entrepreneurial or not, and you can only pass on one lesson to your kids, to your children, out of all the things you've learned, what would that lesson be?
- [82:45]
Tim Gulari
Wake up early and make your bed. It's the only thing that matters over time because perspiration always beats inspiration. And the best companies take time and So I think people that are, that are, you know, that are. That have the juice to go at it day by day, because some days are great, some are not, right? And then, so give yourself the time to be successful. And the second is, you know, do the dirty work. You know, make sure that you're, you know, learning the skills, calling on your customers, talking to investors. That's the make your bed part. But you know, that that's, that's the, that's the easiest. That's a good start to your morning.