The 10% Bet That Built a $12B Company | Howie Liu (Airtable)

26 May 2025 · 1 h 39 min

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In short

Podcast Episode Notes: The 10% Bet That Built a $12B Company | Howie Liu (Airtable)

Overview In this episode of HD in HD, host Henrique Dubugras interviews Howie Liu, founder and CEO of Airtable, exploring his entrepreneurial journey from his early experiences to building one of the most powerful no-code platforms in the world.

Key Topics Discussed

Introduction

  • Background of Howie Liu and Airtable's significance in the tech landscape.
  • Early experiences that shaped Liu's career as an entrepreneur.

Early Life and Influences

  • Howie's family background and immigrant experience.
  • Impact of parents' work ethic on Liu's mindset and ambitions.
  • Liu's early fascination with technology and the internet, including:
  • Creating a Pokémon website and selling items on eBay.
  • Interest in sci-fi literature and its imaginative possibilities.

Education

  • Experiences in high school and the college application process.
  • Choice of attending Duke University and the transition to college life.
  • Howie's involvement in extracurricular activities that fostered his interest in technology and entrepreneurship.

Early Career and Internships

  • Internships and the quest for real-world experience.
  • Cold-pitched algorithm trading models at a career fair.
  • Interning at companies like Bear Stearns and Crowdflower.
  • Learning through practical experiences and solving real-world problems.

The First Startup

E-Tax

  • The journey of founding E-Tax, a CRM solution inspired by a personal need.
  • Lessons learned about market fit and the importance of solving significant problems.
  • The acquisition of E-Tax by Salesforce and subsequent experiences there.

Transition to Airtable

  • Howie's insights gained from Salesforce and the decision to create Airtable.
  • Emphasis on building a platform that empowers users to create business applications without needing extensive technical knowledge.
  • The importance of identifying a large problem space with substantial market potential.

Key Lessons from the Journey

  • Problem Selection: The significance of starting with a meaningful and expansive problem.
  • Adaptability: Importance of iterating and learning quickly from failures.
  • Execution Beyond Scale: Understanding that scaling a startup requires different strategies than established companies.

Key Takeaways

  • Entrepreneurship requires resilience, creativity, and the willingness to explore various avenues and ideas.
  • Real-world experiences, networking, and mentorship play crucial roles in shaping a founder's path.
  • The size of the problem being addressed can significantly influence the startup's potential for success.

Conclusion

  • The discussion highlighted Howie's journey through challenges, discoveries, and his vision for Airtable, paving the way for future innovations in the tech industry.
  • Future episodes are anticipated to delve deeper into the Airtable journey and the intricacies of building a successful tech company.

Connect with Us

  • Howie Liu: [Twitter](https://x.com/howietl)
  • Henrique Dubugras: [Twitter](https://x.com/hdubugras)

Production Credits This episode was produced and distributed by [Atomik Growth](https://atomikgrowth.com).

Time Stamps

  • 00:00 - Intro
  • 01:20 - Introducing Howie and Airtable
  • 02:10 - Early life and family
  • 07:33 - Early tech experiences
  • 14:13 - Building Websites
  • 32:18 - Dreaming big
  • 34:07 - Middle-Class Entrepreneur Theory
  • 35:55 - High school experience
  • 44:57 - College applications
  • 56:40 - Duke University experience
  • 1:05:10 - High-paying jobs and internships
  • 1:09:23 - Neural networks and quant trading
  • 1:16:10 - New internship
  • 1:22:02 - First startup and lessons learned
  • 1:34:22 - The birth of Airtable
  • 1:38:27 - Outro

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These notes encapsulate the richness of the discussion while providing an organized overview of Howie Liu's entrepreneurial journey and the key insights shared throughout the podcast episode.

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Transcript

Automatic transcript. May contain errors.

0:00Entrepreneurship by its very nature is anything but linear. If it was so linear, everybody else would be doing it. When you play Jenga, you don't really know which ones are wiggly and like which ones are going to collapse the thing. If you don't test lots of little things with lots of little like touches, you're just going to go for it and you're probably going to lose. The first startup I chose was actually a 50 % good solution, but for a smaller problem that affected fewer people and just wasn't as big of a breakthrough. The V1 of Airtable, I would say like probably only solved the bigger problem we were going after by like 10%.

0:2710 % of a massive problem that affects every single business and that every business is willing to pay lots of money for. Even the 10 % good solution was actually good enough to get like initial product market fit and a lot more of it than that first product. If you pick the right problem, you can make more mistakes along the way, but you'll have much more upside and outcome to make it worthwhile.

0:55This episode is brought to you by Brex. a brand I'm proud to have co-founded and one that's shaped by the same journey many of you are on. Brex has everything startups and fast-growing companies need to make every dollar count, from modern corporate cards, banking, and treasury, to accounting, automation, travel, and expenses. Over 25 ,000 companies, including DoorDash, Scale AI, and Anthropic, spend smarter using Brex. Hi, everyone. Welcome to one more episode of HD in HD. Today, we have Howie, the founder of Airtable. Airtable is the easiest platform for you to build apps for your business from small businesses all the way to businesses like Netflix.

1:36So let's say you could build like a easy inventory management system or content management system for your business. Airtable is a$10 billion business and we're going to go from Howie's story all the way how he got to Airtable. This episode, unfortunately, we have so much to talk about that's going to have to be split in two parts. I talked to Howie today about part one, which is the story from his childhood all the way to founding Airtable and excited to record of him in some later day, the part two, where we're going to go through the entire Airtable journey from the beginning. So listen in.

2:09So I grew up in Texas. I was born in Texas. My grandparents actually were all Korean, but they moved to China from Korea during World War II. And like many other ethnic Koreans, They ended up settling down there. My parents were both born in China. And then after meeting in China and then moving to the States, I was born in Texas. So they were in China. What did they do in China? So all four of them actually became academics. This is during like, you know, kind of the 60s, 70s era. And all became professors at different universities. My mom's parents were in Beijing. My dad's parents were more in a northeastern region of China, very cold.

2:45And yeah, they just kind of all settled down and like immersed fully into the country. And why did they come? One of my parents come to the States. You know, at that time, like I think, you know, there was a huge amount of appeal to, you know, coming to the U.S. I mean, obviously there still is, but, you know, it was clearly the best place to be, you know. And from an education standpoint, from an economy standpoint, like, you know, it was the place that everybody wanted to be. And so my dad was able to get a basically a Ph.D. to be sponsored by Texas A &M, of all places, in College Station. And then was able to come over, get the visa and then eventually get citizenship through that.

3:26It was, I think, a good university for his interests, which were in agriculture, cotton research, but also kind of a random place to end up. Growing up, I didn't know any different. So the U.S. that I experienced was all through the lens of this college town. So your dad is saying it's agricultural research. Where's your mom research? So my mom studied civil engineering actually at a school in China. But when she first moved over, she wasn't able to use the degree, basically. And there was a language barrier. Neither of my parents spoke English very well. And so initially, she actually went and worked a lot of minimum wage jobs just to support the family.

4:05So like, you know, working at at one point, like a Chinese restaurant, actually at one point McDonald's and like literally like the frying the fries kind of a job to then like, you know, being basically a seamstress and like sewing monograms for a local apparel shop. until later she ended up getting another undergrad degree from Texas A &M. Before that, she was taking some night courses, et cetera. But from then, she was able to go and get a white-collar job locally and then other places around Texas. Until then, it was all of these pretty manual jobs. Interesting. And what did you think of that?

4:44Did you notice it? I definitely noticed it. I mean, it was the McDonald's job. Like I remember like going to McDonald's a lot at that time and actually really liked and still like McDonald's. You know, we get like the healthier options like the, you know, the burger, but not the fries, no soda. But, you know, I think one, I saw the incredible work ethic, you know, and both my parents worked hard. But, you know, my mom, especially these were like really grueling jobs. Right. It's not easy to go and do that and then, you know, come home, watch the kids, you know, help with schoolwork for me, et cetera.

5:17And so I think, you know, the most profound thing was just the level of work ethic and like tirelessness that she took to her jobs. And how do you think that like, you know, you saw that like hard work and you're like, hey, I want to do that, too. Is that kind of like the conclusion you had? I don't know if it was such an active choice. I think it was almost just subconsciously imprinted on me as like the default mode. You know, like if you're going to do anything, you got to just do it with with with high effort. And also like failure is not an option. You know, like there was never a moment where, you know, that my parents ever said, like, you know what, we're just not going to try anymore.

5:59Like we're going to, you know, just quit. Like it was every single day in, day out. Like, let's go and keep doing this, even if it's really hard and you're tired and like, you know, you wish you could go and rest more. But I think having that level of grittiness was was just, you know, almost the obvious default to me. And when you were growing up, did you feel kind of rich, poor or middle class? Like what was your perception? Definitely poor. But, you know, I think, you know, Texas and this hometown in Texas in particular was like it wasn't a place that had a lot of, you know, especially extreme wealth.

6:37You live in New York, you live in SF, you live in LA, and you'll encounter an extreme range of wealth from people who can afford to buy entire islands to people who do work minimum wage jobs. And I think in Texas like that, and in this town in Texas in particular, I think the range was a lot more compressed. I think the highest paying jobs in that town were probably being a lawyer, local lawyer, being a local doctor, et cetera. So there wasn't as much range. And I don't think I fully understood exactly what investors or entrepreneurs really did until much later. But even amongst that range, we definitely always felt like we didn't have that much.

7:23And we would get our clothes at Target or on sale from JCPenney's and so on. And that being said, you know, I think you make of it what you will. And I think it built for me like a lot of like scrappiness. And so early on, I was like really enamored by the internet and like, you know, it was free. Like, you know, once you got your dial-up connection, like everything on the internet was virtually free, right? Like you didn't need a credit card to go and do stuff and play with games or watch, you know, these like internet streaming, like Flash movies or so on. And I even like, you know, figured out eventually like, oh, wow, like maybe you can make money on the internet and, you know, build websites.

7:59I had a Pokemon website that got like five hits a day, which which paid off like point oh one cents in ad income. Or like later, you know, I set up an eBay account using my dad's, you know, kind of information initially, which he agreed to because you couldn't sign up, you know, under 18. But but, you know, started like figuring out how to sell, you know, baseball cards and that kind of thing there. So, you know, I think for me, it also gave me kind of this scrappiness and hunger to figure out like, OK, how do you go out and like make something from nothing? When you were a kid, let's say like, you know, primary school, were you kind of, what were you into?

8:33Like, maths and sciences? Like, what was your... Yeah, I mean, I definitely liked math and science. You know, I was pretty good at it. I think partly, you know, it's because my parents, especially my mom, like, you know, spent a lot of time when she wasn't working, trying to give me like, you know, free advice, free tutoring on that stuff. You know, I also liked sci-fi a lot. So I would read, you know, we'd go to the library, we'd check out like a big bundle of books, like all the sci-fi books. I think for me, it was like a really like great way to kind of feel like the world was more expansive than just this one town.

9:10And we, you know, we couldn't afford to travel all that much at the time. So that was kind of cool to kind of have certain outlets to kind of go and explore. Like I said, like, you know, computers and the internet like became like a really big fascination for me once we got our first uh um i think it was around maybe third or fourth grade possibly earlier i remember it was a um an acer computer it was like the cheapest model they they uh they sold at walmart and i think it was a amd k6 processor with 133 megahertz so whatever that tells you about the uh the era um but uh but i remember you know it was like windows 95 you open this thing up.

9:53It came with like some default games built in. I think it even had like pinball, you know, and you could then like install your own games. Right. And they would, you know, there were like free trials. Um, so it's like the original freemium model, uh, was, uh, what was it called? Freeware. I think you could just like download these files. Now, sometimes they might be viruses, but like, you could also just download these cool games for free. And then like, you know, 20 minutes into playing them, it would ask you to pay. Right. Yeah. So you were into like, kind of sci-fi? What were your favorite sci-fi books?

10:20I really liked, there was this whole series of basically unofficial, but published Star Wars, uh, you know, continuum sequels, right? So they're kind of like fan fiction, but they were like full books. And then, you know, there was this whole like universe that had been thought out of like what happened after all the movies and like all these new planets and characters. So I really loved those, those books. Um, I think I liked a of the fantasy genre as well so like the lord of the rings type books i you know i think any of the books that had something like really interesting from like a conceptual standpoint so here here's what it's like to go into different universes um here's what it it's like to you know travel through time like just like these conceptual plays on what is reality and like you know uh what what could be an alternate way of thinking about the world uh were there a lot of other kids from asian descent to your school?

11:14I mean, there were a decent number for what otherwise would have been like, you know, random, you know, mid-sized 100 ,000 person town in Texas because of the university. So there were a lot of, you know, people whose parents had come in either to study at the university or even to teach at the university or to work with the university in some way. And so it was a little bit more cosmopolitan than probably the average 100 ,000 person Texan city. but it also wasn't you know it wasn't nearly as diverse as you know say like if you grew up in New York City or San Francisco and did you feel like when you were growing up like what what do you think is like kind of things from the Asian culture that like were impacting you when you're growing up it was different because obviously you know in Asian culture there there's like the stereotype of the tiger parent which is very actually true you know in many cases and I think you know it was uh it was true in your case for sure uh you know and i think it was somehow comforting to see that even though it was still a minority uh experience for for uh you know for kids at you know the schools i went to that there were other kids who had similar experiences right so like i wasn't literally the only one or even like you know i think the the type of of food that uh you know my parents would make at home and like we didn't cook a ton but you know my mom would try to mix between like cooking like some, you know, more Asian, you know, inspired meals, we'd sometimes make Korean barbecue at home on our grill.

12:42But like, you know, she would also try to, you know, learn how to make American food, like, you know, lasagna, and like spaghetti and meatballs and that kind of thing. So I think feeling that sense of like, we are, you know, we are trying to immerse as a family and embrace, like, you know, American culture and traditions, We watch all the American movies, but also like, you know, we're not, you know, fully immersed yet. And we're trying to learn it, but also, you know, trying to uphold some of the values that maybe are distinct. And like when you're, did you feel American? Did you feel kind of half-half?

13:19Like what did you like kind of like, you know, feel? I think I felt not fully American, but pretty American. Like, you know, I mean, I was born in Texas and I grew up being exposed to like, you know, all of the American culture and the music and like the TV shows. And like, I actually didn't end up speaking much Korean at all. And now I speak none of it. And even like Mandarin, which is my parents, you know, primary language with each other. you know, I was okay at it. But then, you know, it was very clear, like by later that English was my main fluency. So, you know, I think I felt more American than I did not.

14:02But it also was never, like I never fully felt like 100%. So and you were in this town, like your entire life in college? Is that kind of like? Yeah, yeah. And okay, so then let's, let's get to the computer stuff. So you got into computers, you got your first one, you said you were, it was like probably third grade. So, and I was young for my grade. So yeah, maybe like seven, eight, seven, eight. Yeah. It was internet already. You already had internet, everything. Yeah. So I remember it was like slow internet. Uh, we didn't even have 56 K with the first computer. It was slow. It was like 33.6 K.

14:34Um, but it was dial up, you know, we had CompuServe and, uh, we only had one phone line at the house at the time. So, you know, it's like, if you were on the internet, if I dialed up on the internet, like nobody could use the phone, right? Or if they picked it up, it would be like, you'd hear the static crackle, it would drop all the time. So yeah, it was like, you know, very immature internet. And what do you remember was the first stuff that fascinated you of the internet? I think just the idea, you know, going back to that feeling of like, wanting to see the world beyond, you know, our, like, few mile long city of 100 ,000 in Texas, like, it just suddenly felt like wow like there's all these people out there and i mean early internet was like very personal in nature right i'm sure you had some like big sites like the yahoo's and the excites etc uh but there was also just a lot of like homegrown websites right like you could go and find somebody's like pokemon fan page and it was very personal like it just felt like you know it's almost like going into somebody's like eclectic house and seeing all their weird decor and their like weird design choices and like their weird interests kind of laid out like very literally.

15:46And this is also the era where like the early, like passionate internet users, like everybody had a website of their own, right? You didn't, you couldn't yet create MySpace or a Facebook profile. So like the way you, you wanted to like have a presence on the internet was you had your own website. And so I think that was really cool just to go and like feel like you could go and like see all these different people and content. And, you know, around the time that the, the web 1.0 bubble is happening, you know, I also was was like really fascinated by like seemingly all of these new like products and services that would pop up right so like there were all these like now in hindsight they were probably venture backed companies but like you know there was um like a website where you could go in and like literally just watch all these like flash movies right it was like an online theater but you know the video wasn't even good enough to be like real live action streaming it was like flash right simple flash animations um like adobe flash yeah and so it was like kind of a janky very lo-fi animation style but it like it was very iconic i think of the time totally like simple flash games the coolest part for me was even that like there were all these services that in hindsight must have been vastly unprofitable but where you could go and like either like click around and play games all day and then earn points and then be able to redeem those points for like real prizes right And so I figured out like, wow, like, you know, I don't remember the names, but like there were, I mean, it was a very popular genre, which it turns out like if you give people free money to play games, like you can get some traction.

17:17You might not have a business model, but like you'll get some adoption. And so I just remember like basically trying to find every single one of these sites where you could go and like, you know, earn points or earn money. And and like, you know, just spending all my free time on them to go and earn like, you know, what were effectively like tens of cents on the hour. But then eventually, if you got enough of it, you could redeem it for something cool. And I think like the coolest things I got were like either like trading cards, like baseball cards, which I could then resell on eBay. So it was kind of a way to like convert it back into cash.

17:51Or even like I think I ended up being able to get like a DVD player, which was like pretty cool. It was like a big physical item. And your parents probably looked at it like, oh, that's like a valid aid. Yeah, yeah. I mean, it's like, wow, like where did that come from? Right. Yeah, exactly. Yeah, no, it's because it's interesting because like, you know, in the early internet, you kind of want it at age. You kind of want to prove to your parents that whatever you're doing, the computer is like legit. Yeah, yeah. It's not a waste of time. It's not like going and just playing games at the arcade.

18:15Like there's something real here and it's happening and it's exciting. And like, you know, I mean, there were some really interesting in hindsight, like products and business models that, you know, like one, I signed up really early on to be an alpha tester for a smell printer, like a physical smell printer. Right. And the pitch for the company, it was DigitSense, like S-C-E-N-T-S. And the pitch for the company was like, oh, we've like, you know, we're going to create this printer that you can put into your house. And then when you're watching a movie, it can like make the fire scene smell like smoke and make the like flower scene smell like, you know, floral.

18:50And they ever ended up never launching the actual product, like probably for many reasons. But I remember like, you know, it was also kind of a cool way to learn about like product innovation. And like, you know, I remember even then thinking about like, is this actually going to work? And like, I'm a little skeptical. I mean, this is like the 12 year old me probably like thinking like dubiously about this, this business model. It's like, can this really exist as a business? And it turns out, you know, like it couldn't. But yeah, you know, I think it was like, it was a phase that felt like exuberance in the internet.

19:24And it was both fun, but like also, I think, gave me this, this, you know, a sensibility around like, what's real, what's not. Yeah, yeah, that makes sense. That makes sense. And, you know, I remember, were you part of any forums? You know, not super actively, but I do remember, you know, one, I really liked Neopets once that came about. I was huge on Neopets. Yeah, so I like, there were forums within Neopets. And you could like, you know, there were all these like, you know, different things you could talk about. Like, you know, you could just like eagerly talk about like, you know, which was your favorite type of Neopet or like, you know, offer trades with other people.

19:58Kind of like the Craigslist for like this digital, you know, kind of marketplace. and you could join a guild too which was kind of like a clan you could join like join up with like a team of people and then you're part of like a tribe so i remember playing a lot of those um types of games yeah i was trying to explain i'm you know i met this 19 year old the other day which made me feel very old and i was trying to explain to him like you know it wasn't that long ago you were the 19 year old i know you know founding a company already and exactly the world's the the the roles are reversing these days but i was trying to explain him what forums were and i'm Like, imagine if, like, there was, like, a hundred Reddits or, like, you know, thousands of Reddits instead of having, like, many subreddits.

20:37And depending on, like, you know, the topic, you might go to a different one. And there was, like, social status, you know. I think subreddits are, like, pretty close to what forums were. I mean, I think they probably subsumed most of the forums. Yeah. You know, I guess maybe the biggest difference was, like, A, like, I think the forums were even more niche than the Reddits, right? Or the subreddits. it just felt like there was like very, very esoteric forums at the time. And like there was even more like identity and personality imbued into each of the like anonymized, you know, kind of screen names, right?

21:13Like, so you didn't know who it actually was, but like there was a sense of like, oh, I remember that person. And like this is, you know, their style and their personality and what they care about. You know, it's interesting. I was thinking about kind of like, you know, my experience in the internet and your experience in the internet is that today, you know, you just had a kid and we think about like how much internet we're going to let our kids use. And it's kind of like a topic you're like, I don't know, you know, like there's so much going out there. But if you think about our own backgrounds, so much of it was like the internet, right?

21:43Yeah. Well, I mean, I think one factor that's different is, you know, at that time, the internet was like literally throttled by the bandwidth and on time, right? I mean, like for me, it's like, I couldn't be on the internet literally all the time or else my parents couldn't make calls. So like there was like literally time gated by like the fact that like I had to take over the phone line during that time or like if one of my parents wanted to use the computer or the internet, like we had one computer for a long time. Like so like you had to switch off back and forth. So I think the actual amount of internet time was probably far less than like what some kids have today.

22:17Even in like middle school, they have an iPhone with like always on internet. And I think the second is like the, I mean, even though like there was probably, bad influences at the time as well on the internet. I think the internet was just a smaller place in general. And so I think the number of rabbit holes, like dark rabbit holes you could go down, was probably, I think, optimistically less than. I don't know. There was not a lot of content moderation. It was like, really, you could post anything. I remember there were all these telenovelas in Brazil that kids met someone in the internet that turns out to be, you know, like child molest.

22:56And like my mom was like, don't be an internet because like anyone you meet there is going to be really bad. And, you know, so I don't know. I think it was, but I think people didn't know the risks either, you know, as much as they do today and kind of the downside. I think maybe social media is probably the biggest difference. Yeah. You know, to me, it's just, it's almost like the new normal that like everybody's going to be connected to the internet in some shape or form at a very early age. Totally, totally, totally. And did you learn stuff? Like, did you learn how to code around this time?

23:24How do you build your first website? Yeah, I mean, I think, like, seeing the other websites kind of motivated me to figure out how to build a website. And, like, you know, like, learn some really simple HTML. And, like, it was a product called Dreamweaver at the time. Dreamweaver, remember? Macromedia. Yeah. It was kind of like the Squarespace at the time, but, like, more complicated. I think Adobe bought it, right? Yeah. Yeah, I think Adobe bought Macromedia overall. And then they rolled that in. But I mean, Dreamweaver was a really cool product because like, first of all, it came with its own like a library of little components.

23:55So like, you know, you could build your own HTML website just in like a text file, right? You could type out the HTML. But what Dreamweaver gave you was like they gave you predefined icons, like button icons. And I remember they had some really cool ones. Like one of them looked like, you know, it had like the drop shadow and like it had like a 3D like kind of profile to it, a bevel on it. And so you can make like a really cool looking website. I wonder, was it CSS already or was there some HTML property? I don't recall CSS existing at the time. Now, maybe it was too advanced for me to use it.

24:25I don't know either. I want to say it was all inline styling. I think you just styled things inline in the HTML tags. Yeah. It was definitely a very immature technology at the time. It was like no single page apps. Everything was like you click it and then it takes you to a new page. and like I think the aesthetic of the time was just like put a bunch of stuff on the page right like it was very noisy but in a fun kind of kish way and I kind of missed part of that like I think you know like I said before with the metaphor of like it's almost like when you went to somebody's website you were going into somebody's like slightly messy and like eclectic house that's a really good metaphor and you really kind of learn a lot about them like when you see like oh they decided to like throw this blue button over here and this form like over here and this like traffic counter down here and here's a giant image of like you know like something right here it's like you know it was like subconsciously your aesthetic and your kind of like personality flowed through into your website totally totally totally and at this point right like did you what did you want to do when you grew up right like someone asked you around this time i don't really I don't know if I had thought that far.

25:39I mean, I knew I was very interested in just tech and the internet, all these web companies popping up. And I thought that was really, really cool. And around this time as well, this is kind of a heyday of the Steve Jobs, Bill Gates story, right? Like Apple, Microsoft. You knew about it. You were kind of aware of it. I knew about it. Yeah. I mean, I think they were literally on mainstream news channels quite often. Bill Gates was talked about at some point around this time as the richest person in the world, but also Microsoft is such a cool company in my eyes because they had created Ubiquity and created this technology that everybody uses.

26:18Because I love computers, I was like, wow, they made the thing that allows me to use my computer, like Windows, like Office. That's the stuff I use, right? And so I think there were, and even like, I remember at the time, Microsoft had some early internet plays as well that were actually pretty cool. like there was one game I really liked playing from Microsoft called Fighter Ace. And it was a massively multiplayer, World War II style fighter plane dog fighting game. So you would like go out and like, it was way ahead of its time. But like, I think you could play with like 64 people in real time.

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26:52You could literally be flying around these like, you know, P-52 Mustangs. And the internet was good enough for that. I mean, it was pretty janky. I think at this point, like some people, some early people had like, had cable internet or DSL or at least like ISDN, which is faster than typical, you know, kind of dial up. But I mean, I remember playing it and like I was always at a disadvantage because I had the worst internet connection and like my plane would always like stutter and like by the time I could like try to find the enemy, like they would like jump ahead, like, you know, it was basically impossible to play, but it's still really fun.

27:26And but, you know, like I remember thinking of Microsoft as like this really cool company. It was long before the Xbox, but like really cool company that just had so many things going on. Like they made like this game. They had like a gaming portal. In fact, I remember that like was basically a kind of like the equivalent of maybe Steam today. But like where you could come in and like play all these other games, even from third parties and like find servers to matchmake with. And they had like a Hotmail. It was a really cool time to look up to tech companies like Microsoft that just really felt like they were moving and shaking and building all these cool products.

28:05And, you know, so you're interested in internet, but what was your like mental motto for like money and career at the time? What were your parents telling you like you need to go get college, go to work, make money? Like what was your mental model? I mean, definitely the college part. And, you know, it was like obvious without them having to drill it into me that like I would need to be financially self-sufficient, right? Like I couldn't like rely on them forever for money. And, you know, not because they didn't want to support me, but like, you know, just I had to go out and like earn my own keep, right?

28:36And so, you know, so I think it was always obvious that like, you know, I needed to figure out how to like not just do something that I loved, but also like do something that was like commercially viable as well. And my parents were actually fairly lenient or even encouraging of me pursuing like, you know, kind of a non-traditional path, right? So it wasn't like you have to be an engineer, you have to be a doctor, you have to be a lawyer. It was much more like, you know, hey, like if you really like this tech stuff, learn more about how Bill Gates or how Steve Jobs, you know, built those companies, right?

29:11Like, that's insightful of them. Like, don't just like go and like play the games. Like, you know, if you think it's so cool, like learn like how they made it into a business because clearly it is a real business. Right. So it's not like, hey, this thing can never make money. But like you have to figure out how how it makes money. Because the stereotype of kind of like Asian tiger parents is like you need to be a doctor or lawyer engineer or something like that. Right. Like sometimes I think, you know, I think sometimes like you stick to what you know. Right. And so like if you you know, if your family only knows doctors or engineers or lawyers or that was like what, you know, kind of your own, you know, kind of relatives did or family friends did, then like you're going to stick to the safer path.

29:50I think in some sense, because my grandparents, like I said, were all academics. So none of them had followed the doctor, lawyer, engineer career path. I don't think my parents really cared or wanted me to have to go into academia. And so I think it was almost like from lack of a template to say, oh, well, engineering is what we know to be the main thing. I mean, beyond the fact that my dad did, you know, he was basically a biochemical, you know, engineer of sorts, right, doing doing this, like, you know, research on cotton plants, etc. But aside from that, and, you know, there was never really a sense of like, I have to go and do that or something like it.

30:33You know, I think it was more like they were just agnostic and more open minded to the different career opportunities, especially in the US, right? Like, I mean, part of the point of moving to the States was like, wow, there's so many more types of job opportunities, you know, that you can find out here. Yeah. So, but isn't your mental model like you're like, hey, I just need to be financially sufficient or you thought like, oh, I need to be like rich. It was more like, I know I can't just like go and like do nothing or do something that like doesn't pay the bills at all. Right. So like, you know, even if I wanted to be like a musician, I think it would have been too financially risky for me to even consider.

31:11Right. I did like music. I mean, I played like violin and piano, but I also just like really loved like music, listening to music and so on. I mean, I think like there was a brief moment where like, you know, I learned about like some of the music schools like Juilliard, et cetera. And I was like, oh, you know, that would be kind of cool to get to go and like study music. But I think it was a very easy pruning of that option for me because it's like, but, you know, it's like I can't afford. I literally can't afford to take that route because I think it's too financially risky for my, for my, you know, kind of situation.

31:44And so in a way it was like a, I actually think that like narrowing your optionality can sometimes be a really, really great accelerant to creativity, right? Like constraint breeds, breeds creativity. And so like the fact that like I had to find, you know, a path where, you know, I could at least be financially self-sufficient. and then on top of that like obviously I'm gonna want to do something that like I love and like I you know really find joy and creative inspiration from I think it was pretty obvious to me that like this whole internet thing the tech thing was like you know both really fun and cool for me it's like wow like the thing I love spending all my time on anyways like maybe I could actually work on that like all the time and I do remember like this was the era of like tv documentaries about some of the web, you know, bubble companies at the time.

32:33Right. I remember watching like shows or movies or segments where they would go and like profile, you know, not just the Microsoft and apples, but like also like the excites and like these internet businesses. Positive. Yeah. And like, it was like, here's like these people in a garage who like built excited, like literally built excite out of a garage. And now it's the site that I use every single day. Excite was like, it was kind of like a Yahoo. Uh, it was an early both search and like, you know, they had email etc in fact my first email ever was like you know something i don't remember at excite.com right and i don't know why i chose it but like it was one of like the top maybe four or five at the time uh you know kind of search and email providers it was like them i think ash cheeves uh altavista i want to say um all these like funky names that like you know haven't heard of because you know yahoo gained dominance and then google gained dominance after that right but uh but i remember like just hearing about some of these like, you know, tier two players that were not the Microsofts and thinking like, wow, like, you know, that sounds pretty fun.

33:40Like you get to like, you know, build a website and actually make that your business. When I was growing up in Brazil, I didn't see I only started seeing that when I got TechCrunch for the first time. Yeah. Which, you know, I'm a little bit younger. So TechCrunch was in my teenage year. And I think I've got kind of like a version of that through there. But, you know, I think it's awesome that media covered that stuff because it inspired, right? Like a whole generation of entrepreneurs. But I have this theory, I'm curious to your thoughts, that like, I think that like the middle class breeds the best entrepreneurs.

34:14Because you're kind of like have enough constraints that, you know, like you're saying, that forces you to, you know, and the motivation to kind of want to see the world. but at the same time you kind of have enough comfort that you're not going to like starve you know like you can always go back to your parents house to like eat if you really need to and live and stuff like that yeah i mean i think well you know i didn't consider my upbringing middle class like maybe it would be a stretch to call it like lower middle class um but we definitely didn't feel like comfortable right like all the time and so you know i think for me at least data point of one the hunger of like there is no safety net like actually you know there's a scene in the movie Gattaca, where like, um, basically, you know, this, this, uh, main character and effectively his like genetically, uh, crispered like sibling, they like they're, they're swimming out in the ocean and they have to swim like miles and miles and miles.

35:08And they're basically competing to see who can swim the furthest. And supposedly his crispered, you know, kind of sibling is like genetically superior. Right. But the main, main character actually wins. and when they get back, they're like, you know, the other one's like, how did you make it? Like, how did you swim that far? How'd you beat me? And the first one was like, like I knew that failure was just not an option. I like, you know, I just kept going and I did not even think that turning back was an option. And so I think there is something to that where like the level of grit and just perseverance and be able to push that extra mile, like for me at least was in part motivated by knowing that like there is no easy fallback yeah yeah no for sure for sure for sure and so because and if you think if you ask like your colleagues and teachers you know in high school like was this guy gonna be super successful what do you think they would say you know i think it really depended on which teacher like there were some teachers that i really like felt like i mean they were they were kind of like very um non-traditional.

36:13Because I think if you're a traditional teacher, then I don't know that you foster, like, you know, a very rigid curriculum is not necessarily conducive to fostering like an entrepreneurial spirit in kids, nor do you even know really how to evaluate that when you see it, right? And so I think there were some teachers that were just kind of more like, you know, by the book. And I don't know that they necessarily saw anything like particularly different in me. Like, cause I, you know, like I was a good student, not like the best actually. I was never like perfect at academics. Um, but I was like good, but like, you know, I think the, the real place where I felt, you know, like more passionate and creative, uh, maybe than average was in the extracurriculars.

37:04Right. So like, you know, if I could do something like that, you know, was was more creative in nature right you know and there weren't a whole lot of outlets for that like we did have um like we had a programming team basically it was a very small niche team even for for that you know kind of nerdy subculture at the uh school uh for reference it was like much smaller much less known than even like the math you know club right uh or the spelling bee or whatever but you know i i joined that that group and like we would actually go and do like competitive programming competitions um and and there was a teacher there who was like ioi kind of style not i mean not literally but like probably similar but yeah you you would go and like we'd have like programming meets where uh you know regionally like you would all physically go there in like a bus and then you know show up and like they would give you a prompt assignment and then you have to spend like three hours figuring out how to like solve this problem with a computer right you could program in your environment and then run the code and make sure it worked etc but um but i think the teacher who sponsored that also taught like the one like kind of programming class there and uh you know i remember like there you know i was able to kind of like show a little bit more differentiation and just like show off this thing that like i was really interested in and had been doing like kind of on the side and it's like wow like this thing that i just thought I was doing for fun and learning on my own is actually like legitimized in this actual thing here.

38:36Like that was the first time where I felt like. It's validation. Yeah. It's like, this is not just like a weird hobby that like I have, but like there's an outlet for it. And like, you know, people think there's, there's a real, you know, kind of value to being good at this. It's okay. So if you look at it kind of like through your kind of childhood through high school experience, right? like and you were to try to dissect the things that most probably helped you or were most impactful to your and your later success like yeah what would you say easily and by far you know i think it was the exploration of the internet and like the the kind of like you know what what effectively was like taking an analytical view to all the different types of products and services popping up the internet, like, where's the internet going?

39:27What is the like, getting a real good feel of the internet and just, you know, web companies of the time. Because I think, you know, when I learned how to program, that was key. But, you know, for me, the programming was always in pursuit of building something useful, right? Like, I mean, I liked somewhat the math problem of like solving hard, you know, algorithmic questions with programming, but that was never my like strong suit, strongest suit, or like the thing I like was most passionate about. It's kind of like a cool gimmick almost on the side. But what I really cared about was like, can I build a cool product that people can actually use?

40:08Right. And so I think for me, like, you know, it was more of the product thinking, like, how do I solve a problem with software? With the internet? Programming was the tool. Yeah. Programming was the tool. So, you know, like trying to build like useful apps. And then later in college, like some of those apps, like just because, you know, I only knew the problems I was, you know, immediately exposed to as a college student. But like, how do I go and find a summer sublet? Well, it turns out Craigslist is really hard to use and it's all text and you can't like filter and sort the way you want to.

40:37And so what if I like scraped Craigslist and then did a mashup of that onto a map and then made it really, really easy to like filter and sort and find like, you know, the like exact sublet criteria that you wanted. Now, it turns out that would be a very niche business if I ever tried to like make it a real product. But like at least it solved a real problem. And I was learning how to build a single page app and a rich JavaScript experience, not just for the sake of it, but to solve this actual problem I had. But when you talk about solving problems and products, was there already some sort of business orientation at this time?

41:16Or no, it was still kind of like, I just want to build cool stuff that people use. No, I mean, I definitely wanted to build a business. Right. Like so like I really wanted to find the intersection of like a cool space that I was personally passionate about. I also wanted to build like cool tech. Like I think I was enamored by like new technologies. So like when single page apps and like JavaScript became a thing, like I was super interested in that because like, wow, it's so cool that like, you know, with Gmail or Google Maps, like the way you use these products is totally different than like the precursors.

41:46Right. Like, you know, MapQuest, you have to like click like on one of the arrow buttons to pan around on the map and then wait like 20 seconds for a new map to load in. And so it's just like it was really hard to use to actually like navigate a map. Whereas Google Maps, it's like you could just click the thing and drag around. Like I thought that was so cool. And then the idea that like, wow, like maybe I can like build something like that as well was just really interesting. So I like the tech aspect of it. But then I also really wanted to build something that like could be commercially viable.

42:16You know, maybe going back to the point about like, you know, for me, that had to always be in the back of my mind. Like it was not an option to not go and find something that could fund, you know, my own living costs at the very least. So and then now looking back, right, and you have your own kids now or what are the things that you think your parents did that you would like replicate to them? I mean, I think it's like really hard to carry over any playbook, you know, when the circumstances are so different. Right. So I think my parents had to have this insane, you know, kind of work ethic that whether intentionally or not, and probably, you know, yes, intentionally, you know, kind of very much carried over into me.

43:03and I think that was a function of absolute necessity, right? Like they had to do it to survive, right? And keep going. And they knew that I had to do it as well if I wanted to survive, right? And so I think, you know, fortunately for my children, like I don't think they're in as dire, like a survival mode. Quite the opposite. Well, you know, I mean, it's all a spectrum, but I think, so I actually think it's in a way like a gift to pass on to them, like the luxury of being able to have more freedom, right? And have, you know, more of a fallback. And like, will that mean that they're not quite as like, you know, insanely hungry and driven to have to go the extra mile and like, go until it hurts to keep pushing on?

43:51Maybe. But I also think like, that's a trade off that might be, you know, better for their happiness and like, you know, fulfillment in other ways. Right. And so like, I think it's all trade-offs on like what you have to start with, like, you know, and if you have more optionality, like you just get a different set of options. And then also like what you're optimizing for where, you know, like I had to optimize for something that was like, you know, a business that can make money and could like pay for my, my life. Right. You know, whereas my kids hopefully can like, you know, have more freedom to like explore things that they're truly passionate about.

44:27And like, even if it doesn't like immediately make a ton of money, like in the near or even medium term, like that might be okay. And you think you're going to be a tiger parent or no? No, I mean, definitely not. I think like, I think, um, yeah, I mean, I think again, I think the tiger parent playbook is maybe necessary and, and even like, you know, uh, the only option in certain circumstances, if you want to like survive and thrive. but you know like there are other playbooks now available. So how is college applications it like super stressful process process for you? No I mean like I think the one is always so because I was already like pretty interested in like the extracurriculars and like I didn't you know I didn't care that much about the linear academic path right even in high school.

45:14Like you know I tried to do a decently good job with all my classes and like get decently good grades but I wasn't religious about it. Like, I didn't think like my life would be determined by getting like a 4.0 GPA. Right. Neither did your parents. I think they cared, but like they weren't, you know, they weren't like really aggressive about it. Right. And so, you know, certainly if I flunked out or started like really getting bad grades or like, you know, lost all options to go to a good school like that, you know, they probably would have worried a little bit more. But I think they weren't as extreme as maybe some tiger parents would have been about that, you know, academic process and the college process.

45:54And, you know, for me, I think it was already pretty clear that I wanted to pursue a path where like I kind of got to write my own adventure, right? I was already like excited about programming and like these tech ideas. And I think I just sort of inherently understood that the typical college curriculum would not adequately, you know, kind of equip me to go and pursue that path. Right. Like, I mean, and maybe because like all this tech tech, you know, founding stories that that I read about or heard about, like they were not by people, you know, the Bill Gates and the Steve Jobs and the Excite founders and all these other, you know, kind of like startups.

46:33They were not necessarily founded by people who just like were by the book, had perfect grades. I mean, like I mean, Bill Gates and Steve Jobs were both dropouts. Right. And like Steve Jobs didn't even go to like an Ivy League school. Right. Like you went to read. And so I think just like learning about those stories, it kind of inspired me to be a little non-traditional and like realize like, you know, like instead of trying to like get indirectly to my passion and like my like future endeavor by like first going through this like arbitrarily linear path, like if I want to do that thing, I should just start working on and trying to think about that thing.

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47:42So whether you're just getting started or you're ready to take on the next big thing, Brex has your back. Check it out and see why the world's most innovative startups like Anthropics, Scale AI, and Robinhood trust Brex. So even by this time, I was already more passionate about that thing, the entrepreneurial path, than the typical college process. And so I applied to all the schools. I would say like I did like you know a halfway job on like the application process like you know I didn't spend a lot of time on like thoughtful essays for each school was college confidential thing in your time or no uh I don't remember that one okay it was like the forum that I went to okay like get tips get the real real yeah I don't if it was I wasn't I don't know if I was familiar with it yeah I mean obviously like I looked at the U.S.

48:33news like college rankings and so and there's the obvious ones like harvard sanford yale you know etc are always at the top but you know so i think i just basically went down the list of like top 10 schools applied to all of them applied to also some like you know kind of more close to home schools like university of texas etc where i mean there was a program at the time where like if you went to a texas public university you would get like basically more than a full ride to go if you were qualified right so So you'd pay zero tuition and they would even give you like a subsidy to pay for like personal expenses, almost the way to like bribe you to stay in Texas and go to school in Texas versus like leaving and going somewhere else.

49:17Right. And so, you know, I applied to a bunch of schools, uh, candidly didn't get into like a lot of the top ones, like, you know, Harvard, Sanford, like didn't get in. Um, and you know, it's like, I get it. Cause like academically, if you looked at like my application, it's like not perfect GPA, not perfect SAT score, you know essay that was like okay now we know too that if you're Asian it's harder right like well you know who knows like I mean um yeah I mean I always try to like chalk things up to like things that I can control uh individually but like you know on paper and like the extracurriculars I did I don't think really stood out to the typical like application reviewer right like you know I wasn't going and like you know starting all these amazing you know kind of out of school programs I was building like programs and websites, but like there wasn't even a place to put that on the application, right?

50:09It's not like you could link to your portfolio of like, wait, but look at this really cool website I built, right? And even if you did, like I think at that time, like the reviewers would have been like, who cares? Like, what is this? And so, you know, I just think like the things I cared about and the things that I was working on really just like did not like did not fall into the heuristic, you know, the college application process. but for better for worse, you know, Duke was like one of the good schools, like the better schools that I did get, did get accepted to. And, you know, frankly, like I liked the brochure, like I didn't get to visit, you know, before going.

50:46It looks beautiful. But yeah, I mean, it's like the, the, the pamphlet was like beautiful. It looked like, you know, Harry Potter basically, you know, the architecture was amazing. There was like actually a very misleading picture on the front of the brochure that showed Duke in the snow. Turns out it virtually never snows in North Carolina, especially in that city. And so it was like a completely misleading photo. I was like, oh, my God, it's going to be amazing. And, like, you know, there's going to be, like, real winters with snow. But, you know, it was also, like, a good school. And so ended up just, you know, taking that one.

51:19Like, thought about, you know, a few other options. But took Duke and, you know, kind of showed up on day one without quite knowing what to expect. And when it happened, were you like just happy or were you like kind of pissed off that you didn't get into the other ones? Or, you know, what was your emotion? I think I felt for like a split second, you know, you never like getting rejected. Right. I mean, it's like there was that like symbolic thing in the mail where like, I don't know if this happened if you were applying internationally, but like they would physically send you either the acceptance package, which was big, like a physically big package or the small one, which was like they didn't want to waste the extra paper.

51:56to tell you didn't get in, right? You would literally get like a tiny envelope, like effectively a postcard saying you didn't get in or a big pamphlet if you did, right? And it was so symbolic of like, you know, you would just open up your mailbox every day and like either you got the little one and you're like, oh, okay, well I know what it is or you got the big one, right? And so I think, I mean, you know, there definitely was a little bit of a letdown like getting the small ones from the top schools, having a little moment of like, you know, maybe like insecurity around, you know, is this going to like affect the rest of my, you know, career trajectory?

52:31Like, should I have worked harder on like the academic stuff instead of all these like silly, like on the side programming pursuits that like didn't really matter to the college application process? You know, like have I made like, did I make the wrong set of choices? Right. Like, should I have worked harder on getting in to the right school? Because then maybe like if I went to one of the good schools with a great brand name, like my path would be guaranteed, right? Like, you know, I'd be guaranteed an amazing job. And, but you know, like Duke is, is also a good school. And so like, I, I wasn't like that worried in that, like, I knew that, you know, it was still a good school.

53:07I would still have like, you know, some jobs or like a lot of jobs as an option, even if the entrepreneurship thing didn't work out. and and I also like I think I was like 90 percent still confident in you know my interest in pursuing this like non-traditional path right so like it didn't really phase me that much because I was like okay well you know would have been cooler if I got to go to Stanford or something or MIT especially because you know they both had more of a tech focus but you know like I'll make the most of it and like I mean I'm already doing this stuff on my own like I don't need to rely rely on the school to do the thing that I care about.

53:44So like, what's the difference? Like I'll have my laptop, I can just work on my stuff, like wherever I go. Totally, totally. Obviously, it didn't hurt you a bit, you know? Yeah, I mean, who knows? I mean, like, it's always hard to like, you know, extrapolate what would have happened if, you know, something different in life happened. Like, what if, you know, you had stayed at Stanford, right? Like, you didn't drop out, right? Like, who knows? I mean, it's hard to imagine you doing much better than how you actually did, but who knows? Maybe you would have started a different company right after.

54:14You never know. Yeah, you never know. But I would say you're obviously already in the 0.001%. So maybe you would add one more zero to that. Yeah, I do think there is a disadvantage potentially of falling into the trap of a very good linear path. It's kind of like the corporate ladder where at a very big company, it's like, oh well but like they just keep giving me like a promo one after another and i'm a tiny cog in a very large machine but like i'm getting strung along you know and i think um and it feels like you're giving up something right yeah yeah exactly it's almost like gamified to where like you feel like you have to go through those motions and so i do think it's like you know a lot of the people who i know who did go to like one of the top top schools you know or even like went to duke like got very tempted by like the typical pathing of like okay like you go to these good schools your default job out of college is investment banking or consulting and like within each of those there's like a very clear ladder right like where you go from analyst to associate to like principal to like and you're making money than all more money it's amazing money yeah it's like crazy it's like very 0.1 money but like it's just so linear right and and like i don't think you I think a lot of people who go down that path, they kind of like realize at some point it's like, wait, wait, wait, I got to break the cycle.

55:36Because like as much as like the money is great and the like predictability is great, it's just not what I'm passionate about. But I always say that like it's actually more risky to then take risk at that point in time. Because like in college, you know, like I dropped out. People are like, oh my God, how do you take so much risk? I was like, I felt there was no risk. Like worst case scenario, I just came back to college, you know, like it's been one, two years doing something fun. But if you have like a real career, right, you're like now a VP of an investment bank. Like, you know, like if you drop out, it's not like you're going to come back to the same place, right?

56:05Totally. I think especially once you have, the thing I didn't fully appreciate is that with a family, it gets much harder, right? You know, like now that I have a daughter, you know, it's like my number one priority is making sure she's okay and like being able to take care of her. And let's say like I was now making a choice to drop out of a more linear career to go start a company, but like it would come with great financial risk, right? Like I'm foregoing income. Maybe we don't have that much saved up. Like that would be crazy. Like, I don't, I don't know if I could do it at that point. Totally, totally, totally, totally.

56:40So then, okay. So tell me about kind of like your, your college Duke experience or like, what was it like? And like, how, how did the Howie of college was different than the Howie of like, you know, Texas? I mean, I think in, in some ways it was different in that there were more ambitious people all around, right? You know, obviously self-selecting for like people who were both academically good enough to like make it to Duke. And also like once you're at Duke, like you're kind of like ambitious to try to find like what's, you know, what do you want to do after, right? So people cared. On average, I think people cared more in general.

57:17I think second of all, tech was not very big at Duke. Like even the computer science department, I think was like 20 people per graduating class. So it was tiny. and I didn't actually study CS because I wanted to like actually not just you. Like I felt like I had one college experience. I felt like there were so many other things I could learn and I was also interested in like physical hardware and mechanical engineering, like rocket ships and like that kind of thing. And so I studied that and then also public policy, which was like for me, like something I knew nothing about, like, but I wanted to learn about.

57:49I felt like - I didn't know you studied public policy. Yeah, I mean, I felt like, you know, this programming thing, I feel like I've kind of figured it out. like I can keep making myself better on my own and maybe even faster than if I had to take classes for it. But like this public policy thing, I'm never going to learn on my own. Right. Like I don't understand how government works. I don't understand how policy works. Like I just want to learn it. And that was actually really interesting in a multitude of ways. One is like when you have to think about policy, you have to think very crisply about how the world works.

58:18Right. And like the like real world issues like immigration or tax policy, business policy, et cetera. They're all actually very complex with like second and third and fourth order effects. Right. And so I think it just gave me this like exposure to the messiness of the real world. And then like, you know, trying to impose like reasonable structure to it in the form of policy. Right. And I have a few classes that I really liked. Like there was one on basically intellectual property law. And that was really cool because it was all about like copyright law and like how it's being upended by like recent things like Napster and like the Internet.

58:59And I just found that really interesting because it also tied back into like business models for tech and like Internet. Right. And then like socially, I think like Duke was definitely it wasn't the biggest party school, but it was definitely a party school. And so I think a lot of people had this like mentality of like, it's almost uncool to talk about work or, you know, academics, even though everybody there clearly cared about academics and getting a good job. But it was like everybody had, there was a pretense of like, you can't talk about caring about those things. You have to talk about like just, you know, being social and going to parties.

59:41Were you in a frat? Is there frats? Um, very briefly, but like, you know, it just really wasn't my thing. And like, it was, there was a big like Greek culture at Duke, uh, you know, but also there was like a subculture of people who weren't into it, but still want it to be social and like, you know, friendly, et cetera. So my co-founder of my first startup before Airtable, I met at Duke. Um, and then my two co-founders of Airtable, I also met at Duke. And so like, you know, I kind of think that. Especially if you find people who have a unique and niche set of interests at a place like Duke, like, you know, you have a little bit more of a kindred connection to them than like if everybody cared about those same things.

1:00:25Right. And so for us, like, you know, that kindred connection was like being the few who cared about tech. Like, I think there were maybe less than like 20 people total at Duke my time there who read TechCrunch. Right. This is like early TechCrunch. And so like that was something that we like talked about and related over. And I remember like throwing out, like, you know, just wanting to have people to like, you know, riff on like different like tech ideas with. So that was kind of like the beginning of my friendship with Evan, who would become my first co-founder and then Andrew and Emmett, who would become my next co-founders with Airtable.

1:00:58But yeah, I think like Duke was also, you know, like academically medium hard, I would say, like it wasn't like a complete walk in the park, but it wasn't like the hardest place from an academic standpoint. Right. And also like I cared about grades, but not so much. Like I didn't, I knew I didn't need to have like a 4.0. And so, you know, I think what that afforded me was also like a little bit more luxury of time to go and like continue exploring a lot of like these startup ideas. In fact, I had more time because, you know, with high school, you have like a very rigid schedule, right? Like you go from like whatever it was like eight to four, and then you have like some extracurricular thing, like a science club or the math club or whatever, till like five, they have homework till six.

1:01:44So you really have like very little time afterwards to actually do additional stuff. Right. Whereas in college, it's like, you know, your classes were spread, you know, spread out throughout the day. You didn't have to go to every single class, like some of the big lectures, like you could skip it and catch up and like be fine. And so like, I actually had like just a lot more flexibility in my schedule to go and like pursue my own interests. And in fact, during college, like I prototyped a bunch of different ideas out. I just like really honed my skill in, in building like, you know, apps. But second of all, like I got to go and like test different business ideas.

1:02:20Like I wouldn't go so far to call them like business plans, but like, you know, if I had an idea around like real estate, I was able to go and find other, you know, kids around campus or even like professors who knew something about real estate and say like, hey, like, do you think like, you know, this model could work in real estate where it's like Zillow, but it's for rentals. And, you know, we take a lower fee of commission, but we replace the brokers. So you don't have to pay this like broker fee to find the rental and so on. And I remember that being like a very like fun learning exercise where it was completely outside of like classes.

1:02:59But like, I was going out and trying to like do my own research on the viability of different like business ideas right um and like instead of just prototyping the app first and seeing if it worked i wanted to like first that like is there an eventual sustainable business model there and at this point did you already know you wanted to go into startups and business and that was going to be your thing or not yet that was always like the ideal goal right like even from before college like in high school i knew if i could make that into a real job like make that viable that would be my number one yeah yeah and so it was almost more like i felt like this urgency to prove to myself that i could actually commit to going down that path and it wouldn't be like a completely like bad irrational move right and what was plan b plan b was like take a normal job right like a programming job or um it depends i mean like the interesting thing was like people at Duke really, I mean, very few people actually ended up going into true programming jobs, right?

1:04:02Like, in fact, the irony is like a lot of computer science majors actually didn't want to go become an engineer at a tech company, even like a Google. And instead, like they wanted to go and become a consultant too. Like they were like, they had so bought into the like narrative of like, you got to become a consultant, you got to become a banker that like, they were like, yeah, like I'm smart. Like I'm ambitious. Like I want to be a consultant too. Versus, or even like, you know, the investment banks actually went like Goldman would go and recruit a lot of like the CS grads to become like part of their technology team, you know, but like very few people actually ended up going to like Google or even Facebook, which was so early at the time.

1:04:37And certainly like, you know, even fewer yet to any like smaller tech startups. Right. And so, you know, it was kind of like a pretty non-consensus thing for me to say, like, you know what, like I actually want to not only go into like tech. First, I'm going to try to do my own thing. But if I don't do that, then like, yeah, I think I want to find something that's like tech or tech adjacent, like the closest thing I can find to like doing my own startup so I can learn the most adjacent skills. And what do you think was the pitch that these consultants and investment banks had? And like what you think is the failure in thinking?

1:05:10Money and guaranteed more money if you stick around. Oh, interesting. That's the pitch. That was it. It was like, hey, you're for sure going to make, you know whatever 150k when you come out of school and then you know in five years you can make 300k 400 well i mean look keep in mind like even a 100k salary for a new grad was like a lot of money right it's like you know i think when i was growing up like the idea i mean like the average income even for like a middle class family was like below 100k in my hometown right um like Like 100K would have put you well in the upper middle class bracket and a few 100K would have put you in the upper class, like well in the upper class in my hometown.

1:05:52And so like the idea of like, holy crap, like a new grad can make 100K. Now, sure, you have to work like 100 hours a week and you're going to like literally like get five hours of sleep. You're going to leave the office some days at 2 a.m. and come back at 7 the next day. It's going to be miserable. But like, wow, like, holy crap, it might be worth it. Right. Like, and so I think like one, yeah, like it just seemed like an insane amount of money. And, and then I think consulting was a little different because like, it felt like the allure was like, oh wow, like you get to travel the world. Like you get to go and like every client is in a different city.

1:06:28So you're like always on a plane, which like now I would see as a downside, like I don't want to be on a plane like all the time, but like at the time it's like, you know, especially when you didn't get to travel a lot as a kid, you're like, wow, like I get to like, they get to pay me to like fly to a new cool place like every week. Like, wow. So I think that was the allure. But even like I remember the internships, like the fact that investment banking would pay you, I don't know, let's call it like 10K to 15K for your internship of 10 weeks. Like in hindsight, you know, it's like that prorates out to like a 50K salary or whatever.

1:06:58But like it seemed like a huge amount of money for a college student, right? It's like, wow, like you go make that money and then you can fund like all of your discretionary expenses for like the entire next year. Did you take internships? I did. So interestingly, like, you know, I did a study abroad program freshman year, freshman summer, but also randomly found in Geneva. Wow. Yeah, it was like a Duke program, but it was like actually about public policy. And like we got to go and like do some stuff at like the UN and WHO buildings. Is this the first time you went to Europe? Yes, I believe so.

1:07:37Yeah. So it was awesome. And like, I remember like we, you know, on the weekends, like we could take trains to all the other countries. And like, you know, as a group, we all went to like France and Germany and Italy for like different weekends. That was an awesome experience. Oh, it was amazing. And it was just like, you know, it's like so, it's so epitomized like the college experience that I was looking for in my mind, which is like, wow, like I literally get to go and like see the world. Backpacking through Europe. Yeah, like versus like, you know, having come from a small town where like we just didn't get to travel that much.

1:08:04Right. And so, you know, did that one summer, but the same summer I wanted to pack it in. I actually ended up like getting a random connection to a local restaurateur who actually had this like new barbecue restaurant franchise in North Carolina. He's a really great guy. Tom Meyer is his name. And he had been like a restaurateur before he had like started a wine label that got sold in Target. And so like for me, like as a student at the time who knew nothing about business, like Like it was really cool to get to like basically intern. I think I was unpaid, but like I got to intern for him and like help think through his marketing strategy for his franchise.

1:08:42Right. And like literally at some point I was like designing in Photoshop, like a marketing brochure about the franchise and the benefits of it and like the royalty rate and whatever. And that was like actually a really, really cool experience because, you know, it was like my first time, like actually getting to like work on a real business with a real business owner. next summer did a different thing that was kind of like non-profit consulting is something i was passionate about like social impact um and the summer after that uh funny thing is like i really wanted to do like a tech startup related internship and there was actually like a few random options which year somehow popped up this is um well the junior year was oh wait so this is like when oh actually so now i remember uh speaking of which there was a brief moment where i was fascinated by like the idea of quant trading.

1:09:32And I thought maybe that could be like a way to combine my programming interests with something that like was more guaranteed to pay bills, right? Because I always felt a little bit of like insecurity around like, if I do a startup, and this is a time when like, it was hard to even raise a small seed round, right? I remember like Google already, like hiring a bunch of people and it's like. Yeah, but I think I also understood like, I didn't necessarily want to be like an engineer that was a small cog in a big machine, like a really big machine like Google right and you know Google was smaller at the time but like it was still pretty big already yeah and and Facebook was you already knew about it or Facebook I think I applied to but I didn't get uh a software internship because I didn't you know like they basically were already skeptical because I didn't have a CS major and I actually remember like at the time it was either Facebook or Google like I did one recruiter screen where the recruiter was non-technical and it was like they basically were just doing a behavioral screen and a resume screen on me and they literally asked me like all these questions like okay do you have a cs major and i was like no but like i know how to program in fact i've taken advanced electives for cs because i like could skip ahead and not have to go through all the fundamentals and like by the way do you want to just look at my portfolio like i have websites of like the single page apps i've actually built yeah right like can you go look at them and they were like no like they just refused to even like go to the url and because they were like they just had a process right the process was like, look at the resume, look for these criteria.

1:10:57I don't blame the recruiter. Like they were just doing their job. They were one of many recruiters were instructed to do a very specific thing versus the irony is like just a year and a half later when I was doing my own startup, the first startup that went through YC, like, you know, I got to meet with like the heads of, or like, you know, directors of product, which I thought was a big deal at the time of like of Google and like of other companies, like, you know, these, these big tech companies. And those people were actually impressed by like, wow, like you built this like single page app, like, like we'd love to acquihire you kind of thing.

1:11:28Right. And so like, if they had just clicked on the URL and like been willing to look at the thing that I had actually built instead of like what I studied, like maybe things would have turned out differently. But, but yeah, I mean, long story short, like, you know, thought about doing that, thought about like trying a quant trading like internship, which you basically, there was no official internship for quant trading, At least at Duke, it's not like D.E. Shaw or Rentech or whatever or recruiting there, especially since Duke was not known for a big and well-known CS department. But I basically had been actually at the time, as another extracurricular of my own, in addition to building web apps, been learning about neural networks and really simple ones.

1:12:12Like these were like very primitive, small scale, two layer or five layer feed forward neural networks. And, you know, they were basically all mostly like it was like supervised learning techniques where you would like, you know, basically give it inputs and outputs and train it on known outputs. Right. And then like back test it on like new data. And so I thought like I basically just stumbled on neural nets in my computer science explorations on my own. And I thought they were like really cool in concept. I was like, wow, like instead of having to like program exactly the logic that you want, you just like show the model like what you want it to do.

1:12:47And it learns the patterns on its own. I thought that was so cool as a concept. And so I actually ended up like doing more with neural nets, including like some mechanical engineering projects to like use neural nets to design airplane wings automatically and then test their performance using a basically air like simulation. And that's a whole separate thing. But like for this internship, I basically ended up going deep into like figuring out like, can I try to use a neural net to predict stock prices? Right. And so I like tried looking at a bunch of different input signals I could use, including analyst ratings, like, you know, obviously like technical analysis indicators on the stock price, etc.

1:13:25And eventually got to a point where like, you know, I actually came up with like a model that like at least on the test train validate data set that I was using showed like positive lift. It actually had predictive value. Now, in hindsight, these things are always tough. I would have wanted to much more rigorously test it before putting real money behind it. Because if you do enough model runs, then eventually you get to the point where you find one that shows good results, even on the validate dataset. Right. Like, but anyways, what I ended up doing was like very naively and maybe like, you know, just like optimistically, I like print created a printout of like my work.

1:14:08Right. And both how I, you know, designed the model training and the inputs and like the pre-processing of the data to feed into the inputs and then showed like the predictive value of this model. and like basically ran it against a few different stocks, right? Where I had the input data, like from the school, we had analyst reports. So like I could get like Goldman Sachs and the other analysts coverage about these stocks and use those as inputs for the model. But I basically went into like, there was a career fair day where all the banks, you know, sent their like recruiting people, right? Like, and it wasn't a recruiter.

1:14:46It was like actually sometimes like an MD from a desk who would go and there'd be like the trading person and the investment banker person etc and just by chance I like just went to like some of these different investment bank booths like literal booths and I like tried to like pitch them on like hey like I did this thing with like you know I'll go trading I don't know if it's like that legit or not but like I'd love to get a job with you guys or an internship with you guys like on on this thing if you have one like here like you can take this pamphlet I printed it out you can take it and if you think it's like real like if you think it's legit, like call me and like, I'll, I'll do an internship with you.

1:15:22And there was actually one firm, Bear Stearns, where there was a guy there who was actually an MD at a trading desk. And he was the only one who like understood anything about like what I was doing. He was like, he looked at this and was like, I'm going to give it to, and they actually had like a quant trading desk there. And he was like, I'm going to give it to my colleague and like, and like, give me your contact info. And he took it kind of seriously. And I remember like, they reached out to me and they were like, okay, we'd like to give you a job for the summer. Like, we'd like you to come work on our trading desk.

1:15:50I'm like, we're going to go work on this. So it worked. And it was like his colleague who was like, actually like the head of this like quant trading desk. And I was like, cool. Like, and I'm going to get paid well, probably. And, you know, so I literally had like, you know, mentally like committed to this. And they were like, yeah, we got you. Like, we're going to send the paperwork real soon. And like, I kid you not, like literally the next week is when the whole financial meltdown. No. And like, you know, I was emailing them and like emailing the guy. And then a week later, no response. I'm like, okay, like, are they, you know, like, and then I see in the news, like Bear Stearns has basically been like, you know, and then like, I read like all the Bear Stearns employees are literally carrying their stuff out of the building with the boxes.

1:16:37It's like, okay, this is probably not happening. And so then I scrambled to try to find like a new internship, but I still wanted to do like a startup thing. I eventually landed ironically or coincidentally, you know, I was asking everybody it was like late now in the game, right? Like there was only a couple months before summer. And, um, I was reaching out to anyone I could think of to like, come up with like tech related, uh, internship ideas. And the one that actually landed was like the restaurateur, this barbecue, franchise owner had a brother who was actually like a senior executive at like a bunch of the big ad agencies and then later at a big consulting firm.

1:17:17And he had just left to start this new ad tech startup and raise some venture funding for it. And the whole idea was like, it was a new form of like psychographic targeting on the display network, right? So if you want to target like a certain psychographic profile for a brand, you could go and like, you know, find those people who were cookied in their network and they're targeted with ads ad tech and they're actually based in like tarrytown new york which is like um like north of manhattan you have to take the uh whatever metro north up maybe like 30 minutes outside of the city and like basically through that random connection ended up getting an internship with him for the summer and so i went there and like they kind of knew i could program they knew i wanted to do tech stuff but they didn't really have an officially defined role for me.

1:18:01So I just went and then they kind of threw a bunch of stuff at me, ended up like building a CMS for them and other like apps for them that they ended up using. Like this was like their main, you know, like creative asset CMS, where like when they worked with an advertiser, they would go and like upload into this PHP app, basically a create, read, update, destroy interface, like on top of a database app that I built for them, where they could track all their clients and like the assets for each client and the campaigns that were going to be run. And it was like, you know, I literally had to learn on the job.

1:18:33It was the first time I learned PHP because. What were you doing in before the apps? So I was mostly doing like front end heavy apps with JavaScript before. You know, I think I had like toyed around with ASP.NET a little bit before. Yeah, wow. I think I knew a little bit of PHP and like I looked at Perl as a backend, but I basically tried to keep my back ends like minimal and I was more interested in like the front end part at that point and so like I would do janky things like even just like preload all the data I needed into one blob like on the front end and then manipulate that versus having to do any kind of heavy lifting uh like any server heavy things but this is the first app I built that was like more advanced and actually needed like to be really deployed and maintained like it was actually their production app, right?

1:19:22And so, ended up, like, taking over a crappy beginning of a PHP code base somebody else had written, rewriting the whole thing, and then, like, leaving it for them as, like, a real app. You know, it's interesting, kind of, like, hearing your story. One of the things that stands out is, like, and I would say it's, like, you know, you see this on Success Entrepreneur is this idea, like, you just, like, did so much stuff that you didn't have to do. You know what I mean? Like, you went and you built this like neural network thing and then you send it to this job you just kind of like you know no one was telling you to do that right like this is like your own kind of opposite of like you know when you follow the very linear path the allure you know is that like it's very obvious there's one next step at every point of the way yeah like the one next step in high school is you got to get into a good school the one next step from college is you got to get a good summer internship at one of the major banks.

1:20:16The one next step after that is you got to get hired back and get the job. And then next step, associate, next step, you know, so on. And I think, yeah, I mean, I think like entrepreneurship by its very nature is anything but linear, right? Like if it was so linear, everybody else would be doing it. And by definition, I think entrepreneurship is like doing the thing that like nobody else does, right? And like finding alpha where nobody else can and then actually building something around it. And so I think like, you know, it's almost like i think of it as you're just testing you know like when you play jenga and like there's all the little wooden blocks you don't really know which ones are wiggly and like which ones are going to collapse the thing and i kind of think of it as like all these different little experiments are like you're getting to like touch gently all these little blocks around and see which one you can easily pull out right like versus which one's going to collapse the thing and if you don't do that if you don't test lots of little things with lots of little like touches like you're just going to go for it and you're probably going to lose right you're probably going to like pull down the wrong one.

1:21:14And so I think you just have to keep like, yeah, you just kind of have to keep like being creative and like trying to find problems and then trying to come up with ideas to solve the problem and testing it and iterating it and validate. I mean, in a way it's kind of like the whole Steve Blank lean startup thing, which like, you know, I feel like it over processes or over process it ties it. It makes it too much of a heavy process or an official process. Whereas like, I think most entrepreneurs I knew, I know kind of do it much more intuitively. The concepts are right. Yeah, the concepts are right.

1:21:43But I think you can apply it too much as a rigid checklist. You have to do it a little bit intuitively. But I think that's ultimately what it's all about. You find hidden alpha. Totally. I feel we're going to have to have a two-part episode here. Come back here anytime. Exactly, exactly. But let's jump a little bit to your startups. Tell me a little bit about your first startup and how did that lead into getting to Airtable? Yeah. So, you know, with the same metaphor of that, like, you're always trying to find little problems and find like the problem that is most movable, that you can do the best job of moving like the Jenga.

1:22:22You know, I think in college, frankly, my, you know, one of my biggest constraints was like, I just didn't get that much exposure to like business problems at large, right? Like, you know, I didn't have a lot of exposure to business in general. I mean, that first like restaurant internship I had was like my first time working in like a real kind of business with a real owner of a business, right, too. A lot of the ideas I tried in college, like I just didn't know enough about real world business problems. When I left school, I mean, there's a longer story about how I actually ended up taking an internship or actually a job, sorry, at a larger company.

1:22:59It was like a consulting company, but had like a tech incubator lab within it. My now co-founder of Airtable, Andrew, was working there and got me an internship there or a job there. And it would have been a cool job because the whole job was going and basically prototyping different app ideas for startups, often venture-backed startups. So it became almost like the outsourced app prototyping firm. It was a very small group, so it would have been fun and intimate. But like I also had gotten an internship at a tech startup, a real startup before I went into before I was going to start at that full time job.

1:23:39And the internship was actually at a company called Crowdflower, which is basically the precursor to scale.ai. Like they kind of did almost the exact same thing, but just like way earlier. And basically, after I completed that internship, I felt more confidence like, you know what, this is actually something I want to do. Like that was a tiny startup. There were maybe three people at the time that I joined. and it gave me the most like viscerally relevant experience of like what it's actually like to be in like a three-person real tech venture-funded startup. And I was like, I really like this.

1:24:08I think I want to do this. And so I ended up like, you know, basically deciding day of my first day of this full-time job, this consulting job to do the startup thing, right? And like, I wouldn't recommend that as a way to like, you know, bail on a job like day of without giving advance notice. But like for me, it was really like that was the moment where I just knew like the day came and I was like, you know what? I just I can't show up to work. I have to like go try to do it on my own. Right. Even though it's risky, I'm giving up this like good job, interesting job, pays well, et cetera. I have to go do it.

1:24:41And so in that split second, I was like, OK, I'm going to go do a startup. The first startup I chose was actually inspired by a problem that I experienced while working at the that like the Crabflower company, which is, you know, I was basically playing a role that was a hybrid of like, generalists do like whatever, you know, like, you know, that's this three person company needed of me, but also like kind of solutions engineer for our biggest customer clients at the time. And some of these were like real, you know, large companies that had been partnering, you know, working with us to basically do like some kind of labeling, data labeling jobs.

1:25:17And I would go and like, understand their use case and then implement like with solution engineering, a solve for it on the platform. And in working with all these customers and also like while I was trying to like meet lots of people in San Francisco, because I had moved here for the first time, like VCs and like, you know, the founders and YC people like I just realized like, wow, like, you know, I wish I had a better way to track both the customer relationships and the personal relationships. And, you know, it turns out like the existing CRMs, which I had basically also taken on, you know, the project at Crowdflower to implement a CRM for them.

1:25:51And I realized like all of them kind of suck. Like I looked at Salesforce, it was way too heavyweight and complicated. I looked at all the smaller ones and they're kind of like too simplistic and not customizable enough. And they also all kind of required a lot of tedious data entry, right? It was like very manual. And so in the insight for the first company, E-Tax, like contacts with an E was basically that like, hey, wouldn't it be great if you had a CRM that was really smart and it just automatically like kept track of all your interactions with people and like what's going on with them, pulled in like their Facebook, Twitter, LinkedIn updates, pulled in your emails and texts and calls with them and just aggregated it all into like a green, evergreen like Rolodex, right?

1:26:33And because I was like, you know, thinking about this more through my own personal lens. What if we started with this as like a more prosumer, individual oriented product first, and then eventually go into like a teams or like a B2B model, right? We built that product, basically, long story short, went through YC, raised some funding, hired a small team. But, you know, at some point realized like, you know, we got some early traction, we actually just started monetizing some new features in the product related to like email tracking and like professional email use cases. But, you know, a year in, we also realized like this is not the way we've scoped this problem is not a big enough problem to be the one, you know, for me personally, like I wanted to work on a problem that could generate like billions in revenue, not just for the money of it, but like, I wanted to create something that had that much scale of impact, right.

1:27:27And that was like, kind of a representation of like, how important is this to the world, right? If it's a very niche thing that people kind of only moderately care about, then like you're not creating as much meaningful impact on the world as if you pick a really big problem. And so anyway, I started considering acquisition offers. And you went through YC with this? Went through YC, yeah. This was like pretty early YC, like winter 2010. Oh, wow. So like Airbnb was the batch right before us. Oh, wow. And I mean, it was intimate at the time. There were only like maybe seven, eight companies per batch.

1:27:58How do you know about YC? So I like, I, you know, I think I read about it on TechCrunch, like literally. And then I found YC and I was reading about YC from its website and Paul Graham's early essays. And actually, the funny thing is during college, one of my ideas was like, wouldn't it be cool if you could like know where your friends are at all times and like serendipitously like meet up with them. And then I realized I found this company called Loopt. That was Sam Altman's first company that was doing the exact same thing. I was like researching them. I was like, oh, man, they beat me to it.

1:28:27But, you know, it was obviously really early for that product concept at the time. It was like, you know, long before even Foursquare. And you didn't even have iPhones, let alone like GPS on most phones. It was like a really janky, you know, technological setup to try to implement that product. But I remember looking into it and then, you know, hearing that was one of the first YC investments. And so, you know, kind of learned a lot about like YC then and thought it was a really cool program. And so, you know, I kind of knew I wanted to apply to YC if I did a startup, you know, after school. So went through YC with the ETACs.

1:28:59We ended up going through this acquisition process. And ironically, you know, as I mentioned, like the, you know, the companies like Google, et cetera, that like literally wouldn't even click on my portfolio a year and a half before now, like, I mean, they were like considering like seriously, like acquiring us. Right. And, and so, you know, we, we entertained a few options and I'm going with Salesforce because I thought that, you know, when I thought about like consumer products, I kind of thought like, well, it's kind of hard to predictably create value in consumer, right? Like either you create something like that just is catchy or you don't, right?

1:29:32And like, you got to just kind of know what's in vogue at the moment, right? And I think that's like really, really hard. First of all, there's like a lot of luck required to it. But also second of all, like if you look at the great consumer founders, like none of them had to go learn from another company, right? Like Mark Zuckerberg did not go and have to learn from Google or Yahoo before it. Larry and Sergey did not work. Yahoo, right? Jerry Yang did not work at some other consumer company before it. So if you want to build consumer, you can just do it. If you want to go B2B though, like, and I'd already started to become somewhat interested in B2B with the CRM thing.

1:30:06And like, also just, I think I love the predictability of it. It's like with B2B, I think if you create real value for companies, like they will pay you for your software, right? Like versus consumer is much more about like, is it just the cool thing? And then you get lots of buzz and attention and then you get the network effects. So B2B appealed to me. And I specifically thought that working at a company like Salesforce was the only way to really learn about B2B and become good at like building a B2B company, right? And so we took Salesforce as the acquisition option and got to work there and learn for, you know, a little over a year while working there, learn from a lot of really great people.

1:30:45I mean, there were, there were smart people at Salesforce that I really got to, you know, asked a lot of questions from and kind of mentored me. You know, my acquisition sponsor was this guy, Alex Dayan, who at the time was heading the support and sales CRM products. Was Brett Taylor there already? No, long before Brett. So Brett had not even founded Quip yet. Quip was founded like after we started working on Airtable early days and then they were acquired later. So long before Brett. And then Alex Dayan, actually my acquisition sponsor, eventually right before Brett became, I think, head of all products.

1:31:19He was like the CPO before Brett became that. But, you know, got to learn a lot. And I think one of the acute insights was, wow, like, it turns out like, all of these different businesses and Salesforce support, of course, had customers across every industry, right? Like healthcare and automotive and like financial services and media. But they all kind of have a universal set of problems when it comes to like the need to store business objects or data and then to create, you know, workflows around it. And one special case of those objects and workflows are customers, right? So hence CRM. But at the time, Salesforce was also pushing their platform, Force.com, for non-CRM use cases.

1:31:59They ended up kind of pulling back from that and like kind of more leaning into the customer record, you know, as the kind of main thing. But, you know, at the time it was like, there was this interesting opportunity that they were discovering around being able to kind of universally solve a lot of different business application needs with a single platform, right? With all these different layers of abstraction, like the data model and the logic layer and the interface layer. And I basically looked at that and thought, wow, like that would be a really interesting problem to work on both because like the scale of impact and like the TAM is so big, like so many business applications could be built on a good business apps platform.

1:32:37And also, I think the thing that I can do really well is now think about like product UX, modern product UX, right? And at the time, I was also really interested in like the tech of like real-time collaboration. And like specifically, I'd started like trying out Node.js, which was dramatically easier to do like real-time concurrency with the client. My first business was all built on Node.js, actually. That's awesome. I mean, it was kind of like Wild West in the early days. There weren't a lot of good design patterns and frameworks, but it was so much better in many ways than like the precursors, which were like there were these frameworks built on Python and Ruby on Rails, right?

1:33:14Like Event Machine on Ruby and like Twisted on Python. They were horrible, really, really complicated to work with. And so Node actually made it a lot easier to reason about real time and concurrency. And so, you know, basically I was interested in that tech. and then I thought like wow like a really cool application of that tech would be to create like a very modernized and this is the first time you made money right yeah the salesforce acquisition made a little bit of money like a lot comparatively to like like you probably give you like some comforts around like wow like I'm not gonna like I have a safety net for sure exactly yeah I mean it was like I mean I'll just put it this way like it was like way more than 10 times more than I thought I would make in like a year of working at like even the like well-paying jobs right like you know so it was like wow like I now have like savings as if I had just worked for like 10 to 15 years like at some normal job coming out of college I've now got that saved up right away and you know I can like now have the luxury of being able to like find a really big problem and be much more ambitious um and deliberate about the next thing right and so you know hence we we started Airtable.

1:34:25And interestingly, like, I think this was a moment where, like, a lot of other entrepreneurs were thinking similarly about different spaces, like Dylan from Figma started Figma around the same time. Actually, Figma and Airtable both were built over almost like three years, like two and a half years before public launch, because it just they were hard products to build, right, both in terms of the richness of the product UX, as well as like the complicated backends, like we both have real time collaboration built into the core. And so, you know, we set out to solve this problem of like building a very modern, very intuitive, real-time collaborative app platform that was so easy to use that like it didn't require an admin or a developer to go and use it.

1:35:05You could actually be a business user and just build apps. So, you know, we're going to have to go into the whole details of Airtable in the next episode, part two of the podcast. But, you know, to close it out, when you went to start Airtable and you're taking lessons from the first startup, right? Like what would you say in the acquisition and Salesforce, you know, that whole part of the journey, right? Like what were some of the kind of key lessons you took from those experiences? I mean, I think the biggest thing is like start with the right problem and the right framing of the problem. Because I think with E-Tax, you know, we just kind of had to scramble and we almost just felt like we needed to start a company and we had limited time.

1:35:50Like we literally didn't have savings. Like I didn't have savings. My co-founder didn't really have savings. We literally didn't have much time to like figure out which is the idea we want to work on. And so we kind of had to scramble. We had to apply to YC like, you know, quickly. And then in YC, you have this like 10 weeks to make something real. Right. And so it just was a constant scramble to get something out the door. I think we built a decent product for a decent problem. but like in hindsight, it was a local Maxima problem, right? It wasn't like a big problem. And, you know, the solution we had built was like pretty cool, but like, you know, not nearly as significant a breakthrough as Airtable, which took also a lot more time to build, right?

1:36:32And so I think the number one thing is like, you know, if you pick the right problem, then you'll have, you can make more mistakes along the way, but you'll have much more, you know, upside and outcome to make it worthwhile, right? And there's much more fuel in the sense that even if you only like, you know, the V1 of Airtable, I would say, like probably only solved the bigger problem we were going after by like 10%. Like we only solved for a small subset of use cases across all business applications. We didn't have the scale or the reliability or the customizability on day one, but we solved 10 % of a massive problem that affects every single business, right?

1:37:14And that every business is willing to pay lots of money for. And currently the status quo is paying a lot for crappy solutions that take a long time, right? And so even the 10 % good solution was actually good enough to get like initial product market fit and a lot of it and a lot more of it than that first product, right? E-tax, which maybe it was like actually a 50 % good solution, but for a smaller problem that affected fewer people and like just wasn't as big of a breakthrough. So - And when you worked at Salesforce and saw what the scale looked like, that's when you saw the difference. Scale of the problem.

1:37:46The problem, yeah. Both of the problem. And, you know, I don't think I learned as much from the scale of Salesforce's execution. Because while it works for them at scale, like it's inapplicable to like starting from zero to one, right? You can't take what Salesforce is able to do with their giant machine and just crank out a new product line and sell it to their existing customer base. That doesn't apply at all to a zero to one company. but I think the scale of the problem, when they go and attack problems, they're attacking multi-billion dollar TAMs, right? Like when they launch Service Cloud, you know, in addition to Sales Cloud, like they're picking like a multi-billion dollar potential revenue segment and saying like, all right, we're going to do it.

1:38:25We're going to go full force into it. Makes sense. Howie, this is amazing. We're going to have to do part two, man. I feel there's so much more for us to get into. Yeah, thanks for having me. Thank you so much for coming. Thanks to our friends at Atomic Growth for helping with production and distribution.

From the publisher

Howie Liu built Airtable into one of the most powerful no-code platforms in the world—used by over 450,000 companies and backed by everyone from Benchmark to Thrive to YC.

In this episode of HD in HD, I was joined by the founder and CEO of Airtable as he reelected on the unexpected turns that shaped his entrepreneurial path—from cold-pitching algo trading models at a college career fair, to building software that powers teams at scale.

In our conversation, we get into:

why Airtable took 2.5 years to launch—and why it was worth it

how a CRM for his personal contacts became his first YC-backed startup

what Salesforce taught him about B2B scale (and what it didn’t)

how he talked his way into a quant internship that disappeared overnight

the $0-to-financial freedom moment that let him finally think big

We only scratched the surface on the Airtable chapter, so don’t be surprised if there’s a part two.

ABOUT US:

We’re proudly sponsored by Brex —a brand I co-founded, now supporting over 30,000 businesses like Anthropic, DoorDash, and Scale AI, helping them make every dollar count.

Connect with us:

1. Howie Liu– https://x.com/howietl

2. Henrique Dubugras– https://x.com/hdubugras

This episode was produced and distributed by our friends at Atomik Growth: https://atomikgrowth.com

00:00 Intro

01:20 Introducing Howie and Airtable

02:10 Early life and family

07:33 Early tech

14:13 Building Websites

32:18 Dreaming big

34:07 Middle-Class Entrepreneur Theory

35:55 High school

44:57 College applications

56:40 Duke University

1:05:10 High-paying jobs

1:07:10 Internships and early career

1:09:23 Neural networks and quant trading

1:16:10 New internship

1:22:02 First startup and lessons learned

1:34:22 The birth of Airtable

1:38:27 Outro

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