Tiger Sisters - VC 101: How Venture Capital Really Works (No Finance Degree Needed)

Starting point is 00:00:00 You've heard the buzzwords. Seed rounds, unicorns, venture capital. But what actually is venture capital? How can you start thinking like a VC? VC sounds intimidating like something only insiders understand, but it doesn't have to be. Today we're going to break down the top five parts of venture capital. The first is what VC actually is and how it works. The second is how VCs evaluate startups.

Starting point is 00:00:23 The third is why VC is actually a power game. The fourth is the dark side of VC that no one talks about. And the fifth is how to apply venture capital frameworks to your own career and life decisions. We are the internet's Wall Street and Silicon Valley Big Sisters. And we're a top 10 business podcast on Spotify where we talk about money, power, and love. I'm Cherie. I'm Gene. And we're the Tiger Sisters. And I'm really excited about this episode because I have experience working in venture capital. And we're going to go through real life case studies like we did. at HBS and GSP and talk through examples and also stay tuned because in each section we do have

Starting point is 00:01:17 a mini exercise on how to apply this framework thinking of venture capitalists and take that into your own life. Yeah, I'm also excited to bring in some examples from my time in VC and also from my pre-seed and seed investing I've been doing recently. So let's get into it. We'll get started right after this break. This episode of Tiger Sisters is brought to you by Read AI. Yes, and it's not just another note taker. It's like an AI co-pilot that can read, transcribe, and summarize your meeting notes. It reads the energy and vibe of your meetings to give you the next smart steps. I'm obsessed because it's like having a chief of staff that manages your inbox, your work meetings, basically your entire work life. Yeah, last week I missed a meeting and I was able to type

Starting point is 00:02:01 what did I miss and read AI was able to give me the top takeaways, the key points, and also the sentiment. It was kind of like magic. And it works across Gmail, Teams, Notion, Salesforce, Zoom, basically wherever you do your work. And you know me, I never give apps access to my Gmail because that's super private, but I actually made an exception for Reed AI because I personally know the founder, David Shim, because we used to work together at Snapchat. And you guys might remember we actually interviewed David Shim on season three of Tiger Sisters when he was talking about his new startup, which is actually Reed AI. And now Reed has over four million users. Wow. And they're giving Tiger Sisters listeners a 30-day enterprise trial, which is worth $30 and that does not require a credit card to sign up. We don't know how long this 30-day free offer is going to last. So if you're at all curious, try it right now.

Starting point is 00:02:54 Go to www. reed.a.i slash tiger sisters for a free 30-day extended trial and you don't need to put in your credit card. Sign up through our link because then they'll know that we send you. We're obsessed with Reed AI and we think you're going to love it too. And we're back. Don't forget to like, comment, and subscribe because then you get notified when new episodes drop. And also, don't forget to subscribe to our newsletter, which is linked at the top of this description. And if you're listening to this podcast on Spotify or Apple Podcasts, remember to give us a five-star review. It really helps us get discovered and people can find more of our content. Thanks. Okay, Sheree, let's start off with part one. What even is venture capital?

Starting point is 00:03:36 Venture Capital is high risk and high. reward investing. VC companies give money to startups, many of them early stage, for a piece of ownership in their company. Yeah, and I think the key part of that is that they're not loaning the money. They're actually giving the money to buy a portion of that startup. So they're actually buying equity or ownership in the company. If the startup ends up taking off, the VCs win big, but if the startup fails, then they lose all of their money. Yeah, and another big component of venture capital is all about the stages of investing. So there's pre-seed, seed, series A, B, C, D, onward. So, Sheree, can you tell us about the stages? Yes. So you might have heard of these stages

Starting point is 00:04:18 before that Jean just mentioned. They're pretty big. And if you're talking about startups, raising money and valuation, these stages will definitely come up in conversation. And what these stages relate to is basically the size of the startup and the stage of growth that they're in. So if a company is just starting out and they haven't raised any money before, they're basically pre-seed and then you go up to seed and series A. And each stage denotes the amount of money generally of how much each startup is raising. So series A in general can be from like $3 million to $10 to $15 million. And when you get to series B or C, it's obviously much larger check sizes and the stage that

Starting point is 00:05:00 the startup is in, whether they're in growth mode or they're just starting out. Right. And then there's also something that we won't get into too much, but it's called growth equity. And that's kind of the most mature aspect of venture capital investing. It's usually after series E. Sometimes after E, there's like other series, but typically that's when you're into the growth equity sort of bucket. And that's the part of venture capital where usually it's a lot more, I guess, like guaranteed. Stable. Right. It's much more of a stable business. and they have sort of revenues and numbers that they can predict the success of the company more reliably on. As opposed to early stage startups, which is everything before that, they are just starting out.

Starting point is 00:05:43 And sometimes they're so early that they don't even have any numbers at all because they're just an idea and they haven't proven traction or product market fit yet. And as promised, we're going to be talking about different examples, different company examples for each of these sections, just like we do at Harvard Business School for the case studies. And for this one, a really good example is Airbnb. So they raised their seed round back in 2009, and that was a series of around $600,000. And they IPOed 11 years later in 2020, I think,

Starting point is 00:06:16 at a valuation of around $100 billion. So one question, Shari, that people might have, is why would VCs invest in different stages? Like, what is the, I guess, appeal of investing in, precede versus series D. Yeah. So I would say it comes down to specialty. There are a bunch of VCs out there and they usually have, whether it's an industry

Starting point is 00:06:40 specialty like a vertical like healthcare versus B2B SaaS, that's like an industry specialty or VCs can also or and VCs can specialize in the stage of investing. So the tactics in which a venture capital. firm would look at a series A company is very different in how they would look at a series E company, for example. I would also add on that a lot of times those two sort of vectors are related. So the further on you go in the stages, so like series C, B, C, B, C, B, C, B, D, beyond, the more likely you are to specialize in an industry because then you know more information about it and you need to kind of have more industry expertise to, uh, to navigate all the, um, you know,

Starting point is 00:07:28 information and make an investment decision based on that. Yeah. I was going to say that AI was an industry vertical, but honestly these days it's a horizontal because every single company is using AI now or is AI enabled. So that's not exactly a vertical, but maybe like, you know, five to 10 years ago, it was a vertical to invest in. A hundred percent. So I advise a few different startups. And for all the startups that I advise, every single one of them is talking about like, hey, how can we use AI. And that's the questions that their investors are asking them, even if they're, even if they weren't originally intended to be an AI native company. For sure. Every company is using AI now. Yeah. And then one more question. You mentioned the term B2B SaaS. What is that?

Starting point is 00:08:12 B2B SaaS stands for business to business. And SaaS stands for software as a service. And basically, it's a vertical where a startup or a company creates a product for another company to use. So a good example of B2B SaaS, which you'll hear people say a lot, is Salesforce. They're a massive company and they're a CRM, which basically is like a internal tool that companies use to keep track of their customers and different timelines that they need to sell into those customers. But it's B2B is because Salesforce is a business that sells to other businesses. Yeah.

Starting point is 00:08:51 And the reason I had Sheree sort of clarify it is because this term comes up a lot. lot in VC investing, B2B SaaS, because it's a category that VCs really love to invest in because it's super scalable. All you need to do is build software and then sell to more and more people. Not all you need to do, but you know what I mean. So onto the mini exercise for this section, pick one of your favorite startups. It can be something that you read in the news and you can look it up on Crunchbase or if you have access to it, pitchbook. These are two resources that a lot of people who work in the startup world use daily to figure out the valuation of a company and what they last raised at and who their investors are. Now into part two, Gene, how do VCs evaluate startups?

Starting point is 00:09:33 Yes. So VCs evaluate startups based on three main metrics. Team, market, and traction. Honestly, I feel like the first one is probably the most important one. Team is everything. Yeah, I would agree, especially I would say for the earlier stages, because if you're looking at pre-seed or even seed, a lot of times, like you mentioned earlier, they don't even have any customers. They don't even have any revenue. So there aren't really that many stats to look at. You're much more betting on the team and looking at their past experience and saying like, kind of using that as the information that you're gathering and being like, okay, if these people have done XYZ things before, then I believe that they can, you know, execute on the startup.

Starting point is 00:10:16 Yeah, they can pull it off. In many of the pitch decks for early stage companies, one of the first few slides that they have is exactly that. It's of the team, up and some of their credentials where they went to school, where they've worked, because it really signals to the investors some of the training that they've had. For example, like if you are a you know, former meta engineer or former Google engineer, that's like a lot of signaling. That'd be like I was, you know, raised in the corporate environment there and they have a certain level of training and hiring that they passed. So they are setting a higher bar. Yeah. And sometimes actually can work against you in the same way that can help you because I think

Starting point is 00:10:55 a lot of times people try to start a company or, you know, try to raise money on a company. And the VCs will be like, well, you don't have a technical co-founder, right? Like your team is just you who's going to actually help you build. You're going to spend all your money trying to hire an engineer instead of having one that's already on staff. And it's actually really funny because a lot of the problems that end up happening later on in a company are people problems. So if the team is not the right makeup, if they don't have good conflict resolution, That can be a pretty big red flag for investors.

Starting point is 00:11:29 Something funny that I see or that I've witnessed is when there's like a couple who's founding a company together. Like they're married or dating, but that is a huge risk for investors. If something doesn't work out in their personal lives, it might affect the business on a professional level. And then there's always counter examples. Like I think Canva is founded by a couple. That's right. So that one obviously massive success. So it goes both ways.

Starting point is 00:12:00 It goes both ways. And investors will take a look at that and figure out what risk do they want to take on. And the second one is market size. So basically investors don't want to invest in something that isn't going to have a billion dollar, multi-billion dollar outcome. And that's only possible if you have a really large tam, which is total addressable market. So that's a phrase you'll hear all the time in a VC Tam. They'll be like, oh, what's the Tam? the Tam is this, the Tam is that.

Starting point is 00:12:24 But also at the same time, it's kind of gotten so, it's almost like a joke now because the Tam is so overused. And a lot of times people, when they put together a pitch deck for their company, they'll be like, the Tam is $10 trillion because our startup solves problems for all men and women in the world. Like, if you're not putting together Tam that's actually defensible and believable, it'll actually work against you as a founder. Yeah.

Starting point is 00:12:52 I think Tam is super interesting because taking the example of this podcast, it can go both ways. So our podcast, Tiger Sisters, one could argue that it is a pretty narrow Tam in some ways, right? We're delivering like business, career, like personal finance advice for people who, you know, are strivers and who want to get ahead. But then people have also asked us like, how do you increase the tam of that? Like, for example, comedians have a large tam because. they're working with like jokes that are more applicable to everyone, but it might not hit people in a deep way. Right.

Starting point is 00:13:30 So I think you're making a really good point, which is that it's not just about your total addressable market. It's about of the total addressable market, what amount of those people are actually going to convert and be your customers eventually. And the last big bucket that VCs look for when evaluating startups is traction. Basically, is your product working? And do you have product market fit? And that can be measured in several ways, like people downloading your app that you've created,

Starting point is 00:13:55 generating revenue, like month over month, are people paying for your product? Those are just some examples. Okay, time for the mini exercise. So for this one, think about a problem that you want to solve. Think about a company that you could potentially start. Then think about the Tam. Is this a problem that millions of people have? Is it a problem that billions of people have?

Starting point is 00:14:16 And then the second part is think about why you're the right person to, solve this problem because you're the team. Now on to part three, why VC is the power game. Sheree, why is VC power game? So venture capital isn't just about money. A lot of it is about signaling, social proof, access, and warm intros. Yeah, and I think this is why a lot of times VC gets the reputation of being very clubby, very exclusive, very kind of it's all about who you know as opposed to necessarily always being about the merit of the idea and the merit of the team. True. And I think this is especially true when you think about the biggest or the most well-known VC funds.

Starting point is 00:15:00 So think like Sequoia, now A16Z, maybe like Lightspeed. These are kind of very like brand name VC funds where a lot of times the founders will try to get someone from those funds to invest in them just because they know that is a super strong signal that once they get someone from the those funds, all of the other funds are going to pile in. And this whole idea of social capital is also why accelerators, like Y Combinator, are super popular. Obviously, they have a lot of structure and they have ways where they help the startup actually build at an accelerated pace.

Starting point is 00:15:34 But what's also really important is that even getting into Y Combinator in itself is a signal that Y Combinator believed in you. And then at the very end, they have this really big demo day where all of the, you know, VCs come and even if they don't actually come, they look at all the different demos and they watch all the videos. And that's an amazing way for founders to get exposure to all these big VCs. Yeah, because those major venture capitalist firms have seen a lot of success with past companies. So they have like an amazing reputation and having one of those companies on your cap table also signals that they see something in your startup, which could be a success potentially. And so you just use the phrase cap table. What's cap table? It stands for a capitalization table. And basically, it's just a table of all the investors who have put money into your startup. That's why it's so important for many startups to get the right investor because it's not necessarily just about the check or just about the money. And one example that's pretty easy to understand is the TV show Shark Tank. So when people are pitching their startups to the sharks, sometimes they want a certain investor because they bring a specific expertise to that industry that could be super helpful. Like a Mr. Wonderful versus a Barbara versus a Lori versus a Robert Hershevik, those people bring different specialties. Yeah, that's totally true because I feel like if you had a startup that was in the

Starting point is 00:17:02 software space, obviously you would want to go with Robert. If you had something that was in the apparel space, you would go with Damon. If you had something like vaguely related to real estate, you would want Barbara. And then if you have something like more CPG, you want to do Lori, and maybe also in the software space, Mark Cuban as well. Wow, we really know our sharks. It's a good show. It's a good show. It's been on TV for like 20 years or something.

Starting point is 00:17:29 It's actually a really fun show if you're just like a little bit interested in business because there's like enough drama. And it's very grocable and understandable because a lot of the products are consumer package goods or like something that's very physical. rather than like software, which is like a little bit harder to show on a TV show. Yeah, yeah. Scrub daddy. Scrub mommy. Mamasita. Mamasita.

Starting point is 00:17:55 I'm a mommy. Momasita. So we have a really fun and interesting mini exercise for you for this section. It's going to sound a little cringe, but I think it really works and it helps. This is to map your social capital. This is actually something that Stanford graduate students, we're asked to do if you take a class called Paths to Power. Basically, it's seeing who's in your network and are they the right people to help you make introductions? Do you have people who

Starting point is 00:18:24 trust you enough, who know you enough to vouch for you? This is super important in the venture capital world and it's fun to reflect and see where you land in your life. All right, next let's talk about part four, which is the dark side of VC. Dun dun dun dun. So getting investment or money from venture capitalists is a lot of pressure. It's not free and it comes with a lot of expectation. Yeah. And the main expectation is that you're going to grow your company at this incredible rate. And so I think that's why a lot of startups have this sort of grow at all cost mentality where they're going to take all the money that was invested in them by the by the venture capitalists and sort of like throw it into a lot of growth initiatives that might not even be

Starting point is 00:19:07 the best for the company in the long run. So the mindset of spend now, and figure out the business plan later. We have seen those examples with companies like WeWork or Quibi, where they started out really strong, had a lot of funding from investors, but then flamed out towards the end. Yeah, and a big part of this is all about incentives. So in order to understand incentives,

Starting point is 00:19:29 you need to really understand the way that VCs are typically set up. So venture capital funds, they actually invest in a whole portfolio of startups, right? So typically they have like 20, 30, 40, hundreds of startups that are all a part of their portfolio. And what they're really looking for is a very small portion of them to become 100x,000x companies. Those are the sort of like unicorns that you've heard about before. And they already know, or it's sort of baked into their expectation that the vast majority of all those investments that they made are going to actually

Starting point is 00:20:02 go to zero or like close to zero. It's going to be kind of a nothing burger. That's why they're always sort of like pushing the startups to have like a sort of, massive amount of growth, which it works for certain types of startups and certain industries. And for other startups, it really might be kind of actually detrimental. Yeah. And like with the expectation of a company growing 100x or 1,000x, there are certain venture capital firms or investors who have a style of like being on the ass of the founder so that the founder will have to give updates on how their company is doing, how it's growing, where it's performing,

Starting point is 00:20:41 where it's not, and those updates might have to come biweekly or monthly, but it is pressure on the founder to live up to the investment. It doesn't come for free. Right. So it actually, I feel like it sounds very sexy to be like, oh, like I have VC investors or like I just am raised $4 million. Yeah, I raised X million dollars. But it's not always the right move for every type of company actually. And a lot of times if you talk to startup founders or if you talk to even like investors, a lot of times the advice you'll get is actually do not take on investment unless you really, really have to. Actually, at Stanford's Business School, we have a famous class called managing growing enterprises. We just have a bunch of classes that focus on startups, how to build startups in different

Starting point is 00:21:22 stages. And we invite the founders to come into our class to give a retrospective, like what worked, what didn't work, and how would they change their decisions looking back on it. And advice that we've gotten time and time again is that one of the biggest mistakes that they've made is taking funding or taking investors. Too early. Too early or even taking it at all because it added unnecessary pressure where they could have gone a little bit longer. They had runway, whatever it is. And of course it's different for each startup. But like I've seen that and like my pattern matching is basically like it's a huge freaking deal to take investor money because it makes things so much more complicated for your own business and how you hire and just everything that you do operations

Starting point is 00:22:06 wise because then you have the man over you or the woman, but you have someone, you have an overlord at that point. Yeah. And just to put it kind of like a double underline under my point earlier is that they are incentivized for you to be that 100x company, right? And for you to have an exit. Exactly. So if you end up being a 3x company, like you, you know, you make three times the amount of money you put in or five times the amount of money you put in. For you as a founder, that could be incredibly successful and that could be your goal. But to the VC fund, you're basically like an egg, right? That's a, that's a loser for them. So they... An egg? Yeah. Is that a lot? Is that a thing? An egg? Or like a lemon? No, an egg. Like a zero.

Starting point is 00:22:47 Oh. An o' enough. Um, and so that's why they'll be pushing you to do things that would potentially have like a small chance of making you that 100,000 X company as opposed to kind of like encouraging you to necessarily do things that would make you like a 3x or like a 5x.x. growth company. So like you really have to think about the incentives and like even if they're giving you advice, it might be good advice in some cases, but it might not be exactly advice for like if they were in your exact shoes. Yeah, because they are trying to optimize for their bottom line, which might not be the same decision that you would want to make for your own company as a founder. investors investing venture capital it's so much a people facing venture that like you're really putting

Starting point is 00:23:38 your trust into the investor who is a person who has a certain style personality a persona and that will dictate your relationship with them and how stressed how stressed you are it's really important who you take on as investors that's why actually a lot of times if you talk to investors some of them will be like, yeah, we're super hands-off. We have all of these resources for you to use, but we're never going to be forcing you to use these resources, and we're not going to be telling you what to do. Like, we're just here to support you.

Starting point is 00:24:11 Sometimes certain VCs, that's going to be kind of their, like, sales pitch. Yeah. To be like, oh, we're really hands-off. Like, we're just here to be smart capital for you. And, like, we can be strategic and, like, help you with strategy and XYZ and give you resources, but we are not going to be telling you, what to do. And like startup founders will talk to one another behind the scenes to understand how their relationship is with their investors if they are seeking investment from the same people.

Starting point is 00:24:40 Oh, for sure. This is like a little bit of inside baseball, but even within all the companies at YC, there's like a YC sort of an intranet where you can look up all the different investors and you could see all of their reviews like a Yelp from all the different people who have been NYC. So like if you look at, yeah, from all the different companies. So you can look out as B2B SaaS. Just kidding. So like you can look up, you know, an investor like Scooby-Doo and someone will be like, oh, Scooby-Doo. Do not work with Scooby-Doo. Yeah, like Scooby-Doo reached out to me. We had five meetings. We had a term sheet and we were about to sign it. And then they just ghosted me out of nowhere. That's a really bad experience for founders. And they're just basically warning one another.

Starting point is 00:25:24 Yeah. Yeah. It's also a lot about reputation. Yeah. Going back to the original. It's kind of like a burn book. The burn book of venture capital. Scooby do is do not trust this. Beep.

Starting point is 00:25:40 This literal bitch. Yeah. Is the skankiest investor I've ever met. Yeah. So the mini exercise for this section is to think about any opportunity that you have and ask yourself before you take it on, what are the incentives who's involved, and what are they optimizing for? And you really need to reflect and decide if it aligns with your own personal values. So our last part is part five, thinking like a VC, even if you're not one. So this then, I actually

Starting point is 00:26:13 really like this part because VCs are obviously really, really smart. And I think a lot of what they do really well is they have these sort of like tools and frameworks and structured thinking to help them make these, you know, potentially billion dollar investments. So why not have us use that exact same framework and apply it to making decisions in our lives, even if it's not related to raising capital? Okay, so the first one we talked about is taking a portfolio approach. So basically, if you were a VC, you wouldn't put all of your fund into one company. Like we said, they're investing in hundreds of companies at the same time so that they can

Starting point is 00:26:48 actually capture upside without losing it all on one. So this is something that you can apply to your life in like dating, for example. Yeah, they say don't put all your eggs in one basket. And that's why people have rosters. People, huh? People. People. People. People, people. People we know. People, maybe people you know. People we know well. Hmm. Hmm. Okay. And the next thing is conviction over consensus. So something that venture capitalists are known for is basically having contrarian views. So what is something that you deeply believe to be true? that other people don't believe. How do you even apply this to your everyday life? No, basically, what is something that you believe that no one else believes?

Starting point is 00:27:33 And then what do you do with that? You live a contrarian life. Okay, so what's one way that you live a contrarian life, Sheree? I have an answer for you. Okay. You're a creator. Yeah. You like literally move from like a totally corporate background.

Starting point is 00:27:51 And you have all the tools to be hyper successful in corporate. in corporate and you were and then you kind of you know threw it all way to pursue your creator lifestyle same for you babes same for you good on you for living that contrarian lifestyle dude i'm so contrarian she's so contrarian i didn't even realize how contrarian i am or hyper contrarian it's also contrarian that i'm not married whoa hey now and i don't have kids Hey now. I don't know if that was really on purpose, but hey. She's so contrarian.

Starting point is 00:28:26 I'm loving my contrarian lifestyle. That was totally on purpose. I'm so contrarian. I was just like marriage, no way. And then the third thing is optionality. So this is something that VCs make sure to bake into all of their contracts. So for example, the ability to once you invest in a company, make sure that you always get the ability to have pro rata or invest into the next round if you want to. So optionality.

Starting point is 00:28:50 This is something that you should always be looking out. for in your own life. Keeping your options open with your roster. Or like let's say you're applying for, you're doing a job search, right? You don't want to just have one option and then just be like, hmm, binary. I wonder if this happens. Should I take this? No, like you should always be trying to get a bunch of options so that you can do even just for yourself, like have an understanding of the options out there and then make a more informed choice and have like a little make-off situation. Well, the same with when you're applying to schools, whether it's undergrad or grad schools, you want to apply to a wide variety of schools with different acceptance rates because you want to have like a reach school,

Starting point is 00:29:31 dream school, a target school, and safety schools because you never know which ones will work out with certainty. Yeah. So did you apply to a wide variety of business school, Sheree? Just two, Stanford or Harvard or bust. And did you have optionality? I did. I got into both schools. Thank you for teeing that up because I don't get to talk about that enough. Yeah, she's so badass guys. Like, who the hell gets into both HBS and GSB? And as the lore goes, my lore goes, I went to Stanford. So then I turned down Harvard Business School, which is a great tagline that many people will hate me for saying.

Starting point is 00:30:08 I mean, I mean, quite in all honesty, it's like an amazing place to be in to have that decision. Like I never in a million years thought I would. She turned down Harvard Business School. Yeah, wait, can we have a banner running across this? She turned down Harvard Business School. Let's have a banner running across this video right now that says that. What about me? Mine says Goldman Sachs rejected her twice.

Starting point is 00:30:26 Goldman Sachs rejected her twice. That's a good headline for Jean. But I guess it's just a crazy place to be in, but it's just like a funny headline. And I bet Harvard Business School really regrets letting me in now at one point because now I can say it turned them down. I don't know. You just talked about it like five times for free. Okay. So on to the mini exercise for the section.

Starting point is 00:30:46 Think about one bet that you've honestly been too scared to make. write it down and share it with us. We'd love to hear from you guys. And if you use some of these mindset techniques or frameworks that we just shared with you that venture capitalists use, share that with us as well. We'd love to hear from you. Thanks so much for joining us for this episode on venture capital because venture capital really shapes the companies that we work for, the products that we use, and the headlines that we read in the news every single day. If you enjoy this episode, make sure you subscribe so that you can get notifications about when the next episode drops. And also please share it with a friend who's also interested in these topics because

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Tiger Sisters - VC 101: How Venture Capital Really Works (No Finance Degree Needed)

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