VC 101: How Venture Capital Works (No Finance Degree Needed)

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. 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 Sheree. I'm Jean. And we're the Tiger Sisters. [Music]

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 GSB

capital. And we're going to go through real life case studies like we did at HBS and GSB and talk through examples. And also stay tuned because in each section we do have 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 preseed and seed investing I've been doing recently. So let's get into it. We'll get

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Cherie, let's start off with part one. What even is venture capital? Venture capital is high risk and highreward 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 preede, seed, series A, B, C, D, onward. So Sher, can you tell us about the stages? Yes. So you might have heard of these stages before that Gan 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

in. So if a company is just starting out and they haven't raised any money before, they're basically preede and then you go up to seed and series A. And each stage denotes the amount of money generally how 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 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

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

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

series E. Sometimes after E, there's like other series, but typically that's when you're into the growth equity um 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 like 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 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 at a valuation of around

$und00 billion. So one question shar that people might have is why would VCs invest in different

$und00 billion. So one question shar that people might have is why would VCs invest in different stages? Like what is the I guess uh appeal of investing in preede versus series D? Yeah. So

stages? Like what is the I guess uh appeal of investing in preede 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 specialty like um a vertical like healthcare versus B2B SAS 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, 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 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 5 to 10 years ago it was a vertical to invest in 100%. So, um, 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 SAS. What is that?

B2B SAS stands for businessto business and SAS stands for software as a service and basically it's a vertical where um a startup or a company creates a product for another company to use. So

a good example of B2B SAS 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 uh 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. And the reason I I had Sheree sort of clarify it is because this term comes up a lot in VC investing, B2B SAS, 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, on to the mini exercise for this section. Pick one of your favorite startups. It can be something that you've 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, what they last raised at, and who their investors are. Now, on to part two. Gan, how do VCs evaluate startups? 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 preede 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 you're really there aren't really that many stats to look at. You're much more betting on

revenue. So you're really 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 this startup. 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 makeup 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 meta former meta engineer or former Google engineer that's like a lot of signaling that 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 it can work against you in the same way that can help you because I think 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. Something funny that I see um or that I've like witnessed is when

there's like a couple who's founding a company together, like um 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. Mhm. And then there's always counter examples

like I think Canva is founded by a couple. That's right. So that that one obviously massive success.

So goes both ways. 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 VC, TAM. They'll be like, "Oh, what's the TAM?

The TAM is this. The TAM is that." 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 is10 trillion dollars because our startup solves problems for all men and women in the world. Like if you're not putting together a TAM that's

actually defensible and believable, it'll actually work against you as a founder. Yeah, 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 striving with like jokes that are more applicable to everyone, but it might not hit people in a

deep way. Right. So, I think you're making a really good point, which is that it's not just

deep way. Right. 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, 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,

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

start. Then think about the TAM. Is this a problem that millions of people have? Is it a problem that billions of people have? 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 a power game. Sheree,

why is VC a 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.

So think like Sequoia now, A16Z, maybe like Lightseed. 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 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 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.

Mhm. And so, you just used a phrase cap table. What's cap table? It stands for capitalization table. And basically, it's just a table of all the investors who have put money into your startup.

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 Herseic. Those people bring different specialties. Yeah, that's totally true cuz I feel like if you had a startup that was in the 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. Yeah. And then if you have something like more CPG, you would 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. 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 groable and understandable because a lot of the products are consumer packaged 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. Mamaita. Mamasita. I'm a mommy. Mamaita. So,

TV show. Yeah. Yeah. Scrub daddy. Scrub mommy. Mamaita. Mamasita. I'm a mommy. Mamaita. 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 were 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

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 trust you enough, who know you enough to vouch for you?

make introductions. Do you have people who 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. 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 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 we work or Quibby 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 you need to really understand the way that uh 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 thousandx 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 go to 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 in certain industries and for other startups it really might be kind of actually detrimental. Yeah. And like with the expectation

of a company growing a 100x or a thousandx, 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's doing, how it's growing, where it's performing, where it's not.

And those updates might have to come bi-weekly or monthly. But it is pressure on the founder to live up to the investment. It's 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 raised $4 million. Yeah,

I raised X million 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

have to. Actually at Stanford's business school we have a famous class called managing growing enterprises. We just have a bunch of like classes that focus on startups, how to build startups in

enterprises. We just have a bunch of like classes that focus on startups, how to build startups in different stages. And we we invite the founders to come into our class to give a retrospective

different stages. And we 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 um just everything that you do operations 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,

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 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 Is that a thing? An egg or like a lemon? No, an egg. Like a a zero. Oh, like

a zero. An 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 100,000x company as opposed to kind of like encouraging you to necessarily do things that would make you like a 3x or like a 5x 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 peoplefacing venture that like you're really putting your trust into the

capital. It's so much a peoplefacing venture that like you're really putting your trust into the investor who is a person who has a certain style, a 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 handsoff or like we have all of these resources for you to use, but we're never going to be like 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." Sometimes certain VCs that's going to be

kind of their like sales pitch. Yeah. To be like, "Oh, we're really handsoff. 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. Oh for sure. This is like a little bit of inside baseball, but um even within all the companies at YC, there's like a YC sort of uh in 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 in YC. So like if you look at Yeah. from all

the different companies. So you can look Does that count as B2B SAS? 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. Yeah. Yeah.

It 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. Yeah. Scooby do is do not trust this beest literal

book. The burn book of venture capital. Yeah. Scooby do is do not trust this beest literal [ __ ] 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 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 actually capture upside without you know 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 your all your eggs in one basket. That's why people have rosters. People, huh? People. People.

People. People we know. People maybe people you know. People we know well. H. 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 how do you even apply this to your everyday life? No, I

basically what is something that you believe that no one else believes? 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,

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 moved from like a totally corporate background and you have all the tools to be hyper successful in corporate and you were and then you kind of, you know, threw it all away 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.

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. 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. I'm living my contrarian lifestyle.

That was totally on purpose. 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

contracts. So for example, the ability to once you invest in a company, make sure that you always get the ability to have Pratta or invest into the next round if you want to. So optionality,

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 hm binary. Should I take this?

right? You don't want to just have one option and then just be like hm binary. 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 makeoff 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 a reach school, 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 schools, 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

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. And I mean I 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? She turned down Harvard Business.

Business School. Yeah. Wait, can we have a banner running across? She turned down Harvard Business.

Let's have a banner if running across this video right now that says that. about me. Mine

says Goldman Sachs rejected her twice. 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

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 cuz 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 this section. 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 used some

to make. Write it down and share it with us. We'd love to hear from you guys. And if you used 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 enjoyed 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 this

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Bye bye. Hey friends, it's Cherie and Jean from Tiger Sisters. We need your help. We just dropped our very first audience survey and it's actually really important to us. Why? Because we want to create the best content for you and learning more about you helps us to do that. It takes less than 5 minutes to fill out and as a thank you, we're giving away a $100 gift card at the end of the

season to one listener who fills out the survey. The link is in the video description. Please

fill it out. Thank you for being a part of this with us. Tiger Sisters is just getting started.