This is an eye-hot podcast, guaranteed human.
I think that being delusional is necessary to be a founder. You really have to believe I'm going to be part of the 0.01% that is actually going to build a unicorn.
“What advice are people being told about success that you think is outdated?”
I think that college is no longer needed. That being said, I believe that your network is your network and there's no better place to go than college to expand your network. So you're saying go to college, but don't go there for the degree. Exactly. How do you think the best ideas are found?
Ideas are cheap and execution is everything. Hey everyone, welcome back to On Purpose. Today I'm sitting down with Lucy Grow, entrepreneur, investor, co-founder of Scalay I, and one of the youngest self-made female billionaires in the world. Today we dive into the new rules of success.
Why speed has been a greatest advantage and how AI is reshaping opportunity. Please welcome to On Purpose, Lucy. Lucy, I am so happy to be with you here because not only do we know each other a little bit offline. We've been to some pretty crazy places together.
So I saw you last year on Luminara on the yacht trip, which was amazing.
Yes. And then I saw you on my house where we did a fundraiser event. Then I saw you at the Deor part. It feels like our life has just been met. We've been worldwide and now we're seeing each other in Kent next week.
Yeah, exactly. It's awesome, but thank you for having me. Oh no, I'm so excited for my audience to learn from you. I think that right now we're living at such an exciting time where so many young people are driven, they're ambitious, they want to do incredible things.
You've already lived that, you've done it. You're going on to do more. I know you've shared some ideas with me. So I can't wait to get inside your brain today. This is really fun.
Yeah. I wanted to ask you the first question I have for you is, what advice are people being told about success today that you think is outdated? I still think that college is extremely outdated. I think that we're taught to go study and then get a traditional job, but especially
in the world of AI, I think that college is no longer needed. That means that I believe that your network is your network and there's no better place to go than college to expand your network. Because college is really the first time and only time in your life where you're going to be thrown into a world where everyone wants to make friends.
No one knows each other, right? So everyone's open to this like emotional connection. I always tell people like I actually think one of two years of college is extremely useful because that is where you're going to build your network and you're going to build the deepest network.
Because they're most talented friends are always going to get these like multi-million-dollar
job offers straight out of college. But if you're able to have that emotional connection, like everything is sales from retaining your employees to selling them to get you them to join your company. And college is the best place where you can like a really build that emotional connection because everyone is open to it.
After where it's like you make a work out of company you may join like you know different like interest groups, etc, but it's just not at the same density as colleges. So you're saying go to college, but don't go there for the degree. Exactly. Therefore the networking, the groups of people, the emotional connections, practicing things.
And I think colleges are really great places, especially in classes, they'll learn a lot
“and learn how to think, but you should apply those skills to practical skill sets, or”
you should apply the skills that you learn into practical use cases. So I would learn how to think in these classes and then I would start using AI tools, right? And really accelerate what you can do and be that like 10 next executor earlier on in life. How did you get to college again? I went to Carnegie Mellon.
Did you go to college with anyone that you're still friends with? What are your peers doing now, like what else have they done? Straight out of college I had actually hired the smartest people that I met, so like you know my TA, my computer science little, like they had this like it's not a sorority little, but like within this ES program, because they were just like top of their class, right?
So that was a perfect example of like hey this is emotional sales and this is emotional retention. When I had dropped out, I had actually met a lot of people within the college network, not my specific university, but like within the United States through hackathon. So I'm still friends with them and these are people that I've actually invested into after like you know hiring them, they went on to go build their own companies.
Wow. So I think that's just a perfect example of like how they were ready to like you know open up and be friends with me and by maintaining those connections, I was able to hire them as my employees, retain them and support them when they went to go build their own companies.
Wow, that's so fascinating that you were able to not only maintain those relationships, but they've become mutually beneficial for everyone. Yeah. And it's a really unique way to look at college actually because I think right now
“you have the anti college agenda and then you have people saying you have to go to college”
because of the old reason. So it's an interesting one.
I always want to ask you what's a habit that you think ambitious people think is
going to make them successful, but actually is slowing them down or holding them back.
This is actually probably an interesting one.
I think that ambitious people had this mindset like I want to learn from the smartest people because that makes sense, right?
“So they gather all the mentors and they have possible and then they enter paralysis when”
it comes to this is you're making. So they ask all the mentors around them instead of listening to like their own gut and if
I had done that skill actually would have never started because I had a decision paralysis
when I was deciding whether leaves Snapchat versus go build a company. I gathered on my mentors, I asked them like do you think I should stay at SNAP or go do my own thing and every single one of them and I mean every single one of them told me to stay at SNAP because SNAP was in a type of growth stage and it was about to go public. People thought I was absolutely insane given that I was on this extremely special team
with only 10 people and I think I would have entered decision paralysis if I were to have listened to my mentors. So I ended up listening to my gut and optimizing for learning instead because I did feel like my learning had become stagnant at the company. But I think that actually these smart people constantly want to learn from others so they
find the smartest people and they ask almost too many questions. It's better to make an imperfect decision but move forward because you can change your path than to enter decision paralysis.
I feel like any good decision I made in my life has often been opposed to some of the
smart people in my life because you feel it internally.
“Exactly and I think investments are very similar, right?”
Because you have to go against the grain to make a good investment. Airbnb I think is a great example and Uber is a great example. Like no one thought it would work but the investors that thought it was work they went against the grain. And I think that's when the best decisions are made.
Did you have to give up? Did you have equity? Did you give up stock shares like were you giving up like a ton of money too to go and do your own thing? So I was giving up a lot of money.
I wouldn't call it life-changing money for me per se but I think it was life-changing money for other people. It's actually because Snaps best. Seen schedule at that point was like 10, 20, 30, 40 which is a very unique best-teen schedule. So that meant that I was leaving the majority of my equity on table.
Wow, so you would have had to really feel a sense of in a confidence that you had an idea. This goes back to you are like the average of the people you're hanging around with. And because I was in a steel fellowship network and all my peers were founders that had either
raised tens of millions of dollars or had a billion dollar companies.
I really did believe that I could be one of those people.
“I think that being delusional was necessary to be a founder because if you're building”
a venture-scalable business, you really have to believe like I'm going to make it. I'm going to be part of the 0.01% that's actually going to build a unicorn. I do think that there are other businesses like life-stop businesses that are much more easier to become successful because you're not shooting for the stars, right? Like if you're making like less than 100 million a year for venture, that's not great.
But if you're doing that like 10 million a year as an individual like that can support you for the rest of your life. If you were 22, you had no money, no followers, and you felt like you had no connections. What would you do in the next 30 days to change the trajectory of your life? If I were 22, I would actually go live on campus at different colleges because I feel
like I would be young enough to do so where I could pass off as a college student. That's actually how I was able to gain kind of a network outside of just Carnegie Mellon, where I had lived on Mennel Avenue at USC and just hung out at USC as like a student. I was in San Francisco and I was hanging out at Stanford as like a student per se. And when you blend in the college community, you will just start getting invited to things,
whether it's like fraternity parties or hackathons, et cetera. I would also definitely continue to go to hackathons because hackathons are great. It tracks a certain type of student that wants to do something over the weekend that doesn't involve party, right? They are side-quested to build and learn. And when you go to these hackathons, generally all the surrounding colleges go as well.
It's like M-hacks attracted like pretty much all the East Coast colleges. So they'd pen hack. So they'd hack MIT. So you're not only meeting people from that college, but all the smartest students from different universities. So what you were, you weren't pretending to go to other colleges.
You were just hanging out at other colleges. Pretty much, yeah. And so then you got the benefit of building your network in those colleges too. Yeah. Did you do that because it was fun or did you do that because you knew it would pay off in the long run?
Like what was your mindset as a 22, I guess, when you were a college, you were younger than that? What was your mindset as a college student? Specifically when I had dropped out, and this app completely failed, but for the TL Fellowship, I was going to build Door Dash actually. I built Door Dash at a hackathon and then in between the hackathon and when I decided to go
to build a company, Door Dash got built. So I was like, great, I need a twist on it, right? So the twist was, okay, let's have people cook food for other students and deliver it versus restaurants. This hasn't many, many issues, starting from food safety.
It's completely illegal, whatever. But I launched at Carnegie Mellon and it did well, and I was like, great, I need to expand other colleges. So that was a mindset and going to live in other colleges and like, you know, really get
In the community.
So I can convince other college students at these universities to cook food for like their fellow students. And college is a really great place to do it because it's so high density, like you can just make a Patrick Cook. These were example and run around campus and they'll deliver it to hundreds of students.
People were making like $100 an hour, it was great. Wow. That's great. That's very illegal. Don't do it.
Don't build it. People. How did you feel when you create your version of Door Dash at a hackathon? And then you see the real idea happen? Honestly, I think the ideas are cheap and execution is everything.
So for me, it's like, okay, cool, whatever, right, like Uber wasn't the first, but they
executed extremely well. So I didn't like feel any resentment. I was like, okay, cool, like this is a great app I can use, like let me think of something else.
“Yeah, I think that's what's very fascinating about how your chief is like, you wear a lot”
of people think that the idea is the value. And when you see someone do it, you're like, oh, I could have done it. I could have done that. And it's like, well, no, not really because actually what it showed you is you got a good idea.
Someone went and did it already, but that means you could find another good idea. There's literally billions of people on this earth. Like, people have ideas all the time, and like people execute all the time. Like, you can easily hire a developer in India, et cetera, get it done cheap. Now, you can use AI in, like, use loveable, replic, et cetera, and develop your idea.
But execution is everything.
Where do you think young people waste most of that time when they're building their
career? I think young people are wasting most of the time working at these larger companies because they have golden handcuffs. Because when you're smart, you're literally getting paid millions of dollars per year, right? Which is extremely hard to let go of when you want to leave.
They add in stock. They add in cash. They add in bonuses. I know some of the most talented people that I think could have built unicorn companies that ended up just staying at Snapchat for 10 years because they just kept on getting equity packages.
Which I understand from the perspective, because it is, like, you know, life changing money. They're, of course, 10 years. Like, you're making like, what, eight figures? I don't want to say they're sold because the work is still interesting, but they're
trading off what is, like, extremely life changing money, like, generational wealth. And, like, working on something that they want to do, like, that one project, passion idea that they have in exchange for cash. But do you think everyone could be an entrepreneur? I think everyone can be a certain type of entrepreneur.
It just depends on, like, how much a entrepreneur do you want to be? Like, are you trying to build a $5,000 business, like, yeah, anyone can do that. My friend literally prompted a chat to create a business with, like, a $50 budget, and it actually created business that makes, I think, a few thousand a month. Wow.
Yeah. Yeah. The research of found a domain name, it designed a really crappy logo.
“I think that, like, anyone can be an entrepreneur, but, like, what kind of object?”
Like, what level are you trying to, like, shoot for in the sky? I guess the people that you're saying, like, they could have quit their job. And I guess, and golden handcuffs, of course. There's different levels. Yes.
So even where I grew up, I remember, I was trying to leave my consulting job, which felt like golden handcuffs at the time, I was making, like, 45,000 pounds a year. And that felt like golden handcuffs at the time, because I was, like, that at least pays my bills and pays for my rent. I don't know what I do without it.
When someone's in that position, how should they consider the next move? Like, do you just quit and go or lend you? Come up with an idea first, like, how do you think about the phases and trajectory of building something when you have golden handcuffs? Well, I had personally done, was I was working on side projects.
And after I received investor interest, that's when I said, I'm going to quit and go build. I think that when people hedge too much as an investor, I don't think they're serious, where they want the money inside their bank before they actually quit their job. So I would say we're on weekends or, like, you know, after work on side projects, I get some traction, because that traction will turn into investor money, but you don't really
want to tell investors, like, I haven't really quit my job yet, because it will make them
“feel, all right, you can say that, but you should make it known that whether or not you”
get the money, you will quit your job, or at least just say that. I don't know, because you don't want them to think that you're not serious.
I think people always get caught between that, kind of like Cat's 22 of like, do you quit
first and then you find what you want to do or do you find what you want to do and then build it? It is a sacrifice to de-risk, but de-risking does make sense. So if you're able to work on your side projects over the weekend after work, et cetera, like, yeah, you won't be spending as much time with your friends, but you're also de-risking
your life, essentially. And I do think that, like, once you have an MVP with traction, which you don't need to quit your full-time job to get, like, you will be able to fundraise. How do you think the best idea is a found? I think the best ideas are found when you're solving a problem for yourself, because there's
so many people in the world that if you're building for yourself, other people are going to have that problem, and then whether or how large of a company it can be is just a function of how many people also have your problem and how much are they willing to pay. But you'll know exactly what to build, and then you'll be able to use the product yourself
Be able to figure out which features to build, what needs to, like, how to in...
et cetera. So, I think the best companies that I've invested in, and the best companies that I have built have all been problems that I've solved for myself. And that's where people should start. Absolutely.
“I think today everyone's now thinking, how do you build the next billion dollar company?”
And that's almost like the amount of time to...
Yeah, the next billion dollar company might just be, like, a small problem that you're
some very self, but you decide to expand on the idea afterwards. I've heard you say Lucy, that your biggest advantage is your speed. And I want to ask you, what's a decision that people waste six months on in business that they should figure out in six minutes? So I think the thing that people waste the most time on is actually just product development
and design. Because when you go to a large company and you see how long it takes to design small features, it can be months to years. Because they want the UX be perfect, but like a common misconception is that the UX needs to be perfect for product to be adopted, I actually highly disagree.
People will go through bad UX, people will deal with bugs if they want the product badly enough. Like, for example, let's say there's the new iPhone, right? And like, you're checking it out and it just keeps on bugging and it's like, okay, cool. Like, the payment then you go through the payment then you go through.
You're going to keep clicking that payment button like a hundred times until it goes through. Like, you're dealing with the bad bugs because you want the product badly enough.
“So I believe the best thing to do is just release 90%.”
Like, you can design, I think, 90% good UX in one to two days. And then just have them to use build it, ship it. And then see if it's adopted, if it's adopted, then iterate on it until it's a good product. There's very, very few products, I think, that need perfect UX for it to get adopted. Most products out there, like, if people want it, they will buy it.
People feel like they need to build the full product in order to sell it.
But my philosophy has always been like, create landing pages.
Like, if you're building a B2B SaaS product, like, make a landing page and start doing calls. If it's like a low enough price point, see if people enter their credit cards. So like, save a spot on, like, the page. If you're building, like, even a, like, D2C product, I say sell it and then see how much
you actually need to produce. And if you're late on orders, just give the customer another free, like, P-shirt or something. Or whatever your building to make them feel happy and, like, not be upset that the order was late. That way you're actually testing the man for the product before wasting so much money
and so much time developing, just for the flop. So many people I see when they're launching something, they're spending all the time on the logo and the font and the color and all these types of things. And actually you're saying, well, put it out then, see if people even sign up. Yeah, exactly.
And even care about it. And if they do, then you've got all the time and money now to actually go and build the real thing. What's our addiction to perfectionism? Like, why do we do that?
I almost think it's an excuse. I think that people believe that something needs to be perfect in order for it to work. And when it's not perfect, they blame it on the fact that it's not perfect. And I see this with tech founders all the time too, where it's like, okay, cool. Like, we just need to AB test their way into it being perfect for the product to work.
But sometimes a sum of all parts doesn't equal whole, right? You can AB test to have higher sign up rates than like higher, like engagement, et cetera. But then they like, there's only so much that can fix. Like, you probably need entirely new feature, which is not really AB testable. Yeah, I think that it really is just an excuse.
What's the difference between a good risk and a bad risk?
“I mean, I think it's all a function of like, what are the consequences, right?”
I generally believe that a lot of products could not have been created without taking risks. So for example, like, I think Uber obviously didn't really listen to anyone. And they became so big that now. It's just exists. I was actually talking to stripe founders.
And I don't remember what rule they broke. But even stripe apparently broke some rules. And then they just became too big to fail and like, they just had to make it work. So yeah, it's a function of just consequences. But how do you evaluate that when you don't know?
Because I guess we all start thinking, oh, God, if I do this, then the opportunity cost is this. So this is the risk level. I generally evaluate just based on like two criteria, which is like, is this going to be life changing for me? And am I optimizing for learning? Because if I'm not optimizing for learning, I'm just not going to do it.
Because I think that the knowledge I gained doing the next thing, even if I, like, you know, lost a few million
and it's not, for example, like I was going to learn enough being a founder that can take those skill sets and, like, you know, either go get a new job that pays me better and I'll be a more successful my role or build another company. And then the life changing money thing was also just kind of that where I was like, okay, like, this doesn't necessarily change my life. So it's not worth my time. There's something that we can all use in in pretty much any decision.
Always optimize for learning.
That's such a big one because it's almost like we want to optimize for success. But you're saying optimize for learning and that will lead to success, exactly.
Yeah, like everyone always comes like, oh, it's such a big risk to like, you know, quit college or it's such a big risk to like, quit this job to build a company.
But it's not like you are losing your knowledge and skill sets, right? If anything, you come out that are side and you have more skill sets, like, yeah, you might have given up what's called it like a 10 million dollar your job. But guess what, you'll probably get a 20 million dollar your job. And I also think that people underestimate like how much like people want talent, which obviously we saw it with meta right paying like nine figures for AI employees. I think that even if your company fails, if you hired talented people and you yourself are talented, there will be someone that will buy your company for more like then your investors invested in evaluation.
Because they know you want to make your investors whole and they know that you want money.
And for the talent they'll overpay.
I keep thinking about my life and it was much smaller than that, like I said, the amount I was making, but making a pivot.
“Companies were so good at making you feel like, no, but you built a network here, you should stay here like there's such a culture of.”
Making you feel like you're going to fail if you move on. And I think people believe that people buy into that. How do we break out of buying into the fact that we actually think if we lose a $100,000 a year job, then we're going to end up with a $70,000 a year job, we don't think we're going to be able to triple it or quadruple it. Yeah, I mean, I think that is just again, your network is your network and you are the average of the people that you hang around with.
So I was really lucky to bring out with founders that have done it before. So I knew like how it actually went. I was lucky enough to hang out with investors who, you know, they would give exploding term sheets, but they would also tell me, oh, exploding term sheets aren't the thing like at the founder came back, we would just give them the term sheet again people's fear is overcoming their logic. Yeah, because logically it's like why would I not be able to get this job back?
Like if I was valuable to the company, they're going to want me again and let's say for whatever reason to roll a spilled. I mean, companies find rolls for people all the time when they think the person is swiss army knife and like smart and will be able to help the company, they'll like make a roll for that person, right? But also there's so many companies out there that will hire you based off of the fact that like you did great job at like company A, like company B is going to want you and company B will fight for you and like understand it now you have more knowledge and more skill sets.
So they'll pay you more. This is really people's fear overwriting their logic. Everyone says find your passion. What's your take?
“I think you should do what you're best at to have the highest impact on your passion.”
For example, like I really like nonprofits and supporting charities, but at one point in time, I thought like I'm going to start my own nonprofit charity and foundation and you know that might still happen, but also realize like at this age in this state of my life, I'm really good at making money. So my time is probably the best spent making money and donating to causes I care about and being run by people that actually know how to run an organization or foundation. I don't know how to run a charity and like I had actually looked into this.
Like I'm going to start a foundation. I'm going to do X, Y and Z and I realize how much work it is, right? And like how it's like quite literally another full time job. Like maybe when I'm older, I'll like learn all those skillsets and I'll decide like my time is best spent doing that as my passion. But I think optimized for fun, fun doesn't necessarily need to be your passion, but like optimized for like how you can make an impact in whatever your passion about. But that feels hard, right? Because people are like, for example, when I was growing up, I was passionate about soccer. What do I do with that? Because I can't be a soccer player because I'm not good enough. So then what do I do?
But you can make enough money to buy soccer team. Right. So you're saying that it doesn't have to be your career, but you may go build a career doing something else, but then use the fruits of that labor to them be close to your passion.
“Because if you're able to experience your passion, that's what's going to make you happy, right? Like it doesn't have to be your full time job. Well, I guess now music is my career issue, my side class.”
But I just used everything that I had succeeded in and like, you know, the money I had created to go experience music and like live events and that made me extremely happy. I use like what I've been able to create that helps support causes I care about, which is made me extremely happy. I don't think that needs to be your full time career. And like for most people, it's not going to be their full time career because like in certain fields, like even know how talented you are.
Some of it is just luck, right? Like, I'll never really understand the music industry or the acting industry because I've so many talented friends in it.
And it just for what a reason they're not making it. And I really do think it's because there's other factors like network, luck, et cetera, and that. But I like what you're saying that people often say pursue a passion or make it your work, but actually what you're saying is just go work, do the thing and then connect to your passion.
That feels much more realistic for most people.
Like I think for the majority of people, there are very few people who can do what they love and it makes money. But actually being free to the idea that you can do something, not hopefully that you don't hate. But you do something and that something gets you to be able to be closer to all of these things that you love.
“Which I think is a much more genuine, authentic path for most people, like people can aspire to live that way.”
Exactly. And like you said, now you're closer to music, charities. What were you passionate about? Like if you could have done something, like for me, I would have been a soccer player if I could have. I thought it was good enough. What would you have done if you could have? Well, it's changed over the years. So when I was younger, I want to be a singer.
If I realize I'm basically tone enough and I can't sing for my life. So that was out the window. And I remember when I was choosing colleges, et cetera. I was like, it would be really cool to be an FBI agent. Like fight the bad guys.
But then that's unrealistic because I like this tiny woman. And you know, maybe I could learn, you know, comfort skills. But like overall, let's call it unrealistic, right? And I get really passionate about music. And I finally learned, I can actually DJ.
You don't need to be able to sing or play the instruments, et cetera, to be able to DJ. So it's been like a very cool thing that I've been able to do. How do you at this stage in your career? How do you separate self-worth from net worth? This is really interesting.
So I was not a confident person until I went to Miami. And I went to Miami. I just became friends with all these people because they just like my energy. Right? I'll just see standing an elevator and people would come in and be like, well, I fell your energy from far away, blah, blah, blah, blah. It was the first time my life.
I met people that were just like me, cast a sukasa with no questions.
“There's no agenda. And I think in the past, like in LA San Francisco and New York,”
there's always like some sort of agenda people are like, they want to know why was.
It's like, oh, your deal fellow. Let me, let me, you friends with you. Or your founder, oh, you have a fund. Miami was the first time in my life where no one asked what I did. And they just wanted to vibe with me because I gave off good energy. So it became extremely happy there.
And I think my self-worth is based off of that where I, you know, I have a close relationship with my family again. I'm close with my friends. And every time I meet someone like that's a stranger that's no idea who I am. They're just like, wow, your energy is so vibey. Let's dance. And that makes me happy because it's like, it shows people like me for me versus like my net worth.
Versus like, I don't think I had that purity before I had experienced it in Miami. Entrepreneurially in professionally, what something that you thought would go your way, but turned into a rejection or a failure? Honestly, like, I'm not someone that sits in weeps.
Like, I've never really sat in felt sad.
So unless, you know, like a close friend is hurt. Like, I think you're bad news from close friend. But for myself, whenever I face rejection, I'm like, okay, cool onto the next. So I've never felt extremely hurt. One of the more, like, sad ones might have just been
when I was so close to like my top VC choice. Like, I was like, I'm 100% going to get a term sheet. Like, they're whining and dining me. They just flew out to meet me. And then it was just like, out of nowhere.
It was a no, right? And I was like, what in the world happened? Yeah, I was just like, I felt a little bit led on. But also like, I didn't really sit and feel bad about it. I was like, okay, cool onto the next. Let's find a new lead.
Do you think that mindset's integral and important at that level? I think it being an extremely positive person. That's constantly optimistic is what has gotten me to where I am today.
“I think the worst thing you can do is think like, oh, like, the world is unfair.”
Why did this happen to me? Stop thinking that way. Like, everyone is born with advantages and disadvantages. You kind of just have to take what you have and go forward. And if you face rejection, just learn from it and immediately go and fix.
That mindset obviously worked for you. You've made so much money. You've become such a success story. What problems did money take away and what problems stayed or got worse? When I first started out before I had any money, I was like couch surfing all the time.
But I like didn't have anything to pair with. Like, I actually love couch surfing. I was fine. You get to meet a lot of people. Like, I found couch is extremely comfy. I was like to the point where I had an apartment. I had a bed and I would sleep on a couch.
So like, that was like nothing but like any stresses of money went away, right? But I also think that like what it can cause is you become a little bit too comfortable, which is in great.
You've been in so many rooms now with so many successful people, incredible entrepreneurs.
People that you've worked with early days at Snap. What do you think is the most surprising thing you've noticed about the people at the top? Something that we'd be surprised or shocked to know? I think the people at the top are actually not the smartest people in the world at all.
I think that they lack frameworks. And because they lack frameworks, they don't understand a concept of like how the world works.
Which is actually very good because startups are built when you break frameworks
because you innovate, right? Which is why when you take someone in an industry that's been in industry for decades and hire them in, oftentimes they don't innovate because they're like,
"These have to be done this way because things have always been done this way."
And again, Airbnb, Uber, great examples of this. They weren't transfer experts, they weren't real stay experts. So they didn't have a framework of like how things are supposed to be.
“I think that people at the top completely lack frameworks”
because they didn't have decades of experience. And because of that, they were able to innovate but also tell their employees. Like their employees might be like, "That's impossible." And they're like, "I don't care." And their employees might be PhDs and like, "No, literally."
"I've been doing this for 20 years. I have multiple PhDs. This is impossible." And they'll just like, "No, it's not. Go do it." And they will say things like, "Okay, whoever does it gets this like giant bonus, whoever does this gets promoted, et cetera." And when people see that prize, that's when people really force themselves
to break the framework that they know because they're so desperate to like, get that thing that was offered to them. I would say like, when you look at the people at the top, they're not the most educated really. I think that in general they have how you use.
Some of them don't have how you use. But they force them possible to be possible. You're reminding me of that great conversation between Steve Bosnia, I can Steve Jobs. It's a Steve Bosnia goes up to Steve Jobs and he goes,
"What do you even do? You're not a coder. You're not a marketer. You're not a salesperson. You're not an engineer. What do you even do?" And Steve Jobs replies, he says, "Musicians play their instruments. I play the orchestra."
It's such a powerful statement because he doesn't know how to do all
the bits and bobs. He's like, "All I know how to do is put it all together and get it to all work and harmony." But I don't really know everything. And I think people when they're on their journey, they feel like, "I'm not smart enough.
I don't know enough. I should be more experienced." So what's that balance then with nothing about an industry, which is not having a framework as a positive thing, but then what is different about that entrepreneur that you don't know anything about the industry?
“You break all the rules? That's what makes you successful?”
I think it's also being visionary. I think Steve Jobs actually great example of this, where he told his team, "I don't care if it's impossible. You're going to figure it out." Elon Musk has told him to steam this, et cetera, et cetera,
because they like the frameworks to really understand this is impossible and it might have been impossible at the time, obviously innovations do happen in technology and they force their employees to innovate and break those frameworks to make their vision possible.
But I think it's been open to the possibility of things, like lacking frameworks. And then just, I don't want to say, they had knowledge in technology in general, right? But they might not have an expert in real estate
and transportation in industrial design. But I think that you need just enough knowledge and then just enough grit, just enough persuasion to get the smartest people in the room, come in some to innovate. It's almost like having that undeniable belief
that we can find a way. Exactly. And it's almost like we have to find a way because I'm not going to accept anything less than that. Exactly. I can literally tell you like this did happen at Apple,
obviously this happened at SpaceX and look at like Elon now. What is the kind of that leadership zeal or approach can often burn a lot of people as well? All leaders are extremely controversial polarizing. Like there is no leader out there where like everyone loves, right?
But I think that being polarizing makes you interesting and the people that are on your side are going to work their hardest to make you happy
“and like to bring that product idea that you have to life.”
What were the biggest challenges you had? Did you have any friction when you were rising up the ranks and building your company? Where were the points that you hit difficulties? This comes down the hiring to write people and again like all leaders are polarizing.
But we were like all hands on deck. I think that every single company I've been at has been all hands on deck where you're not just going to be doing what your job description is. So at scale, we had like you know the engineers labeling data.
I had my engineers talking to creators and doing customer support because I think that when you are deep into weeds you're going to really understand especially like when you're working with customers you're going to understand like what needs to be built.
What bugs there are, like what's critical, what's not.
So I think it's extremely important to be in the weeds especially early stage and talk to customers and do things outside your job description. Even our investors were doing things outside your job description where they were like on LinkedIn helping us like find new employees
to hire. They were like clean our office for us when we didn't have time to because we were constantly on sales calls. You can imagine that like that can create a very polarizing environment
Because we probably like I didn't get hired to do this
but the right people that you hire are going to be willing to be all hands on deck. Right now in this AI world that we're living in. What are three skills that humans should develop? Knowing that AI is going to be able to do pretty much everything.
“So I think the number one skill they should develop”
is human connection. Like being able to like have high EQ, being able to do sales, etc.
because that's never going to disappear.
AI might be able to reach out to agents like negotiate a contract for you, right? But how you're going to close the deal is through human connection and how you are able to even like win over deals is through human connection, right?
Like so much of it in this goes back to your network as your network is that like things are emotional sales emotional retention. Like even extending a contract for example. So I think that's definitely the number one skill in the AI world.
Number two is I think develop really good taste in like whatever you are doing. Like for example, AI is going to replace a lot of designers but the designers with the best taste are going to be able to pick out.
Okay, this is the best design that this AI has generated. So let's go with this. Yeah.
“And then I think three like figure out how to scale your time with AI.”
And if you're able to do this sooner than everyone else,
like let's say you have an idea and you decide to make an app with AI or you create these spots. And like that helps you scale your time and be like you're using the solution to everyone else. And then you sell that bot to help other people in your role
be 10x more efficient out of your wells. You're going to be able to create that wealth. Before I don't want to say it's too late. But like I do think that AI is going to make a lot of people rich but the people that fall behind it's not going to be great for them.
You are a chatGBT Claude Proplexity. What are you using? I use different tools depending on the use case. I think anything I want to say like consumer related can be anything from like helping me think of like music ideas
to research in like the best totals out there. I use chat and then for anything and our prize business focus I use Claude.
Nothing really beats out Claude and Claude's new design tool
is absolutely phenomenal. And what's cool is that like you know you could literally design something and Claude design and then import it in the Claude code, which is great. Even like little details like Claude is really good at designing
like full scale applications. So like UX UI etc. But if I want like a simple graphic edit that I would normally use Photoshop to do, that's actually better at that.
There's different reasons to use different tools. How is AI changed the way you're hiring for your new companies versus your old one? I actually include AI questions in every single role right now.
And right now I am actually asking my entire team to give take homes to non-technical roles. So for example, with their AE roles, so sales, it's like I want you to figure out how to use cursor, rublet, like Claude code
to create a bot where it's like you take an Instagram profile and guess to me, like how much a person will earn. Because hey, that's extremely simple to do using AI tools. It'd be, I can see kind of how you think based on how you prompt it.
Like what metrics are you looking at? What are you scraping on it internet, etc. to get this number out there?
“I think that every employee needs to be using AI”
to be a 10x employee now. So if they haven't taken the proactiveness to actually do that themselves, I want to see how quickly they can learn over a weekend. Because I do think that like some people
just have the cider haven't been in a role where they let me learn, but it's so quick to learn. I think learning trajectory is everything. So if someone can learn quickly, they can easily become a 10x employee
versus someone that might have had more experience but stagnant and resistant to learning. So I think he comes challenges are really great for this because within 40 hours you can see like a cool like how much did he do. What job do you think looks safe today
or won't exist in 10 years? I think that there are certain creative jobs that look safe today that won't exist in a future. Let's call it like being a like videographer photographer.
That is a very human job. That's not very analytical. It's very artistic, etc. But I actually think that most models are going to be AI generated.
Like a lot of humans are going to license out their likeness. So AI is going to generate a bunch of different videos and photos, editors might still exist, right? Like the taste makers will go in and choose the right one
and edit it to be what it should have been. Certain jobs like that. Like even writers, right? Like AI is going to get extremely good at writing but editing will still exist.
What's the biggest mistake people are making with AI right now?
The biggest mistake we're probably just be assuming
that AI works really well and they're just assuming everything output it is true, right? Like AI is really only as good as a data that you give it.
So if you feed a model like the sky is red it's going to output the sky is red.
“This happens everywhere, even with engineering, right?”
Like if AI makes one mistake and then they continue to create more and more bugs but you trust AI to code for you, that's not great. Which is why right now, like if you take a great engineering of it AI,
it becomes a 100x engineer but if you take a mid-level or an entry-level engineer and give it AI, you're just going to actually end up with a lot of tech debt because they're not fixing the problems that AI is generating. I think the success across the spectrum.
When did you first start learning about AI? I mean, I would say probably started with scale. Scale is the picks and shovels of the AI industry, right? We weren't creating these innovative new foundation models. We were literally labeling the data
so we went out of self-driving car companies. Send us lighter data, images, videos, and we had labels around the world say that's a car that's a pedestrian, that's a stop sign on the road.
That was what we were extremely good at and that's always going to be needed
because it goes back to your model as only as good as a data that you feed it. That was when I really started learning how important data is because even with generative AI, if it generates something wrong and it thinks it's correct, you're going to get more wrong generation. That's not great, which is why reinforcement learning
is always going to be a thing. But yeah, I would say that was probably so back in 2016, was when I first saw understanding AI. You learned about AI in 2016, 50 to 60% of the current US population have used AI at least once.
And that shows that we just feel like AI just came around two years ago.
“What's the thing that people like yourself are talking about right now?”
The world is only going to catch up with in 10 years. You were talking about AI 10 years ago and the average person was not talking about AI. They didn't even know it was coming. Yeah, I mean, 10 years is a really long time. But I think that right now what I'm thinking about constantly
is what's going to happen to college students because like I said, AI can make someone exceptional, really, really great. But when you take someone entry level, AI does their job better. Like, Claude just shut down tables, so it's no longer accessible. But fable is as good as a staff engineer.
It's absolutely incredible.
So if you're a really great engineer, holy crap, you're going to be like a thousand next engineer. And the better you are, the more useful AI is. But again, if you're like entry level and you're using it, like you're not going to be able to utilize it in the same way,
and it's not great. I think in general with new technologies, new jobs are created. Like prompt engineering is not a new job, right? And it's an extremely important new job. So I like now we have a bunch of people labeling that up
because that's a new job and that's a huge industry. For people who don't know what is a prompt engineer do? They basically prompt the AI to output what you want it to output. Okay, so having something is so good at writing a prompt. Yeah, so good at writing prompts, so like you get the output that you want.
Because everyone's just putting in these averages. Exactly, yeah. My best guess is that like AI has actually democratized being able to start companies and be an entrepreneur.
“So I think more people are going to become entrepreneurs.”
Because before you would need a you raise a ton of money than higher engineers and a huge team and then go build the product. And now AI is building products like that for free, really, or extremely cheap.
So I think ideas people are actually going to be able to execute way better than before. Like in the past, like it was like, okay, cool. Like if you're not an engineer, I don't want to invest in you. But now someone that's an ideas person can literally use AI
to generate something and get traction on it and then be able to fundraise. And you can now raise significantly less money to get to metrics that you would need to get to before you can raise a series A.
So because it's a lot cheaper to start companies and run companies, I do think it's going to democratize access to being an entrepreneur. And like that is going to be a middle ground people are going to take when like, you know,
students realize like, oh shit, what do I do? Like, I can't get a job. They're going to figure out how to use AI to start their own companies.
Did you always know you're going to be this successful?
I always knew it's going to start companies. And the reason why is because like when I was younger, I was always just figuring out how to make money and build things. Like I really enjoyed building things
and seeing people use my products. What would you build as a kid? So I built like a virtual pet site. I don't know how I convinced a bunch of engineers designers artists to work for me for free.
So I built out for you. I think I was in like fifth grade or something. Yeah, like fifth sixth grade really, really young. I built like our K-game websites. I built like Twitter bots internet marketing tools.
But what was really exciting to me was just like, it can be like a really crappy website. Like, based off a WordPress, but I would submit it on stubble upon. And I'd be like, oh my god,
there's 10,000 people on my website. Like I just love seeing people use my products. And then I would say like in college, when I discovered hackathons, which is very early on,
like my freshman year as like, I'm going to build a company. Because my first time seeing that there was like so much more to the world than just building internet marketing tools. And I was like, wow, I can build extremely impactful companies
That really change how someone lives their day to day life.
But in terms of being successful,
I think that it goes back to like, probably after I joined the TL fellowship, I didn't necessarily think like, oh, I'm going to be a billionaire. But I looked around and everyone around me
was raising tens of millions of dollars. They were like shooting to really change the world with their companies. And obviously like, I think valuation is a direct measure
of how impactful your product and your idea has been to the world.
“So did I think I was going to impact the world?”
Like, I guess yes, I didn't know to what scale. How does it feel to be the youngest female billionaire in the world? Like, how does that feel? I'm still the same person as I was when I was younger, right?
Like, I think the difference is like, when I was maybe 20 years old, I was literally skateboarding to Barry's boot camp. And now I have someone that drives me to Barry's boot camp. We are still at Barry's boot camp.
But it's still at Barry's boot camp every single day at 6 a.m. I still wake up at 5.30 a.m. every day. I'm still in the office until late.
Like, I always try to be like, when the first people in the office,
I'm going to last people to leave. All the Brittany might have maybe here. What's needed a first, not the last, Lee? What do you think you had that was different about you? That made you design sights when you in fifth grade?
What did you have that people around you didn't have? I didn't have friends. I have to say that. That was like you were feeding it to me. But I had extremely strict Asian parents, right?
So my parents didn't really let me have sleepovers. And then I was in a lot to do sports, et cetera. So for me, I didn't really have friends. I was not cool, right? I was just, I know I wanted to be my friend.
And I wasn't a lot of pets either. So I think it all started really with NeoPats. I started messing around with internet. And then I was like, wait, this was really cool. I want my own version of this.
“That's why I wanted my own version, why I love building things.”
Like, I learned how to use Photoshop pretty early on. Like, I was learning PHP, like how to build WordPress sights and edit them. I don't really know why I had that desire. That was almost like in me. In me, I want to say I wouldn't have been a professional athlete
if I didn't have Asian parents. So I think that was really it. Well, what's for? I was really good at swim. I had a lot of medals.
I was very good at basketball. And then right now, I have Olympic qualifying times on the treadmill on like a very good day. But not in the US. I'd have to like go move the Singapore and come people
Singapore where I have no competition. But I think one of those three. Wow. Still any dreams? Are we going to see Olympic ground in the future?
I have Olympic friends that are a very upset I'm not side-question to be an Olympian. Because they've seen me work out. And they're like, you should absolutely train for Olympics. They recruited actually by Olympic like your training groups.
Really? Yeah. But no, my side-class is currently DJing. Yeah. I love that.
I don't know if you decide to plan on being a parent ever. But like, how do you feel about that? You had strict Asian parents. Do you agree with that? Did it work?
Would you do it the same way? What would you change? Yeah. So I think the thing I would change is that I wouldn't force my kids into a passion.
And my parents actually didn't force me into like my passion. Per se. Like they actually want to meet you a pharmacist. Because they're like, oh, you can work three days a week. Like you'll be a little like fine and good husband.
Get married. And I was like, that sounds like my worst nightmare working three days a week. I would be so bored. I don't know what I would do. So creative didn't happen.
But I think that prodigies are made. And I would want to throw everything at my kids and find what they're passionate about. And I think people are generally passionate about what they're good at. So I would figure out what they're good at. And what they seem to enjoy.
And then really accelerate their development in that one thing, whether it's math, whether it's like being an F1 dresser. Because if you're able to get like a multi-year head start, you're just going to be above everyone else. I love it.
So I don't want to force them into passion. But once I find it, like I wouldn't be the very best in their passion. Lucy, honestly, whenever we spent time together, I laugh a lot, I learn a lot. You're exceptionally sharp and smart.
I mean, I could tell her just how much you thought about the questions that you gave me answers that surprised me or once that I've definitely not heard before. Oh, I'm glad. Yeah. We end every episode of on purpose with a final five.
These have to be answered in one sentence maximum. Okay. So Lucy, go, these are your final five.
The first question is, what is the best advice you've ever heard or received?
I mean, this is pretty simple. But I was in the best piece of advice. I've ever received as just like just ask, as a worst thing that can happen is that you get a no. And I do this for really everything in my life still.
And you have to be able to handle rejection. So be able to handle rejection and just ask. Perfect. Question number two, what is the worst advice you've ever heard or received?
“So I think the worst piece of advice I've ever received is that you need to hire”
executives with decades on experience to have like an adult in the company. Because especially early stage when you have an adult in the company, what they end up doing is bloating your team up. And that's not great for early stage, obviously, because you end up burning a lot more money.
Yeah, it's so interesting, isn't it?
Because you always go through this, like, do you need a young team?
Do you have to bring an adult in? I don't want a young team. Yeah. Very, very. Very probable.
You're very in fact. Question number three, what's something that you learned at 30? Do you wish you knew at 20?
I think when people believe that you're wealthy,
it is a lot easier to move around in this world.
“And I say this is someone that you should take pride in dressing”
and like she and Walmart, etc. I realize how much easier life gets if I just present myself nicer. It opens a lot more doors and this goes back to like your network. Is your network, but you actually do want those doors open oftentimes? And what if people say things like, "Oh, but that isn't philophantic to me,
and that's not real."
And what's your take when people say something like that?
I think there is a way to be presentable and still philauthentic. But it also depends on like, are you down to have that trade off, right?
“But I just remember in the change in how much easier life got”
and the connections I've been able to make since I stopped taking pride in dressing like a hump. Yeah, and like those are great connections I've opened a lot of doors for me. Question number four, who are your entrepreneurial heroes? I actually really admire Whitney Wolf because we all know the story
how she was kicked out of Tinder, right? But instead of sitting and having victim mentality and being sad, she literally went for you and created a direct competitor that's doing better, which is just awesome. I love that mentality of a fighter.
Fifth and final question, we asked this to every guest has ever been on the show. If you could create one law that everyone in the world had to follow, what would it be?
“I mean, this is so basic, but I think just be nice to every human being, right?”
I think kindness makes a world go around. Lucy, go on, thank you so much. As I said, I've learned so much. Look forward to spending lots more time together. Excite to see what you're going to go build next.
Yeah, lots of things. Thank you. Yeah, that's a joy. Thank you so much for giving my audience so much of your time, your guidance, and your energy, and so grateful.
Thank you for having me. It's fine. If you love this episode, you love my conversation with Airbnb founder, Brian Chesky, on how to tap into your creative potential and the number one thing people get wrong about success.
The best people in your life will be people who see potential in you that you didn't see in yourself. And I often wonder, this isn't a heart podcast. Guaranteed human.


