Brent Liang on Co-Founding with Justin Kan, Weekly Moonshots, and Vulnerability in Leadership - E42

· Popular,Thought Leaders,Podcast Episodes English

"The thing about moonshots is, whatever you do, if you do it long enough, you're always going to land at a spot that's higher than where you would originally be. You just heighten your trajectory, and it's super important. I hope that trying to do something that's outside of your comfort zone everyday is a personal development goal for everyone as well." - Brent Liang

Brent Liang is a 3x founder ($1M ARR), recording artist, and the co-founder & executive producer of The Quest podcast along with Justin Kan, co-founder of Twitch.

Born in New Zealand, raised in Shanghai and currently completing his law studies in Australia, Brent started his entrepreneurial journey at 18 making mini podcasts. He built his first company facilitating bail assistance for Aboriginal and Torres Strait Islander youth in 2018, through the LawWithoutWalls program. He then co-founded Chance Myanmar, an influencer-led MOOC platform in Myanmar, and grew it to $1M ARR in 1.5 year. In 2019, Brent started his third company Logieq to help founders hire smarter, and led the first Australian team in 10 years to break into the Hult Prize Accelerator program through Dubai, London and New York to meet with President Bill Clinton at the UN Headquarter. Brent is now working alongside Justin Kan on his podcast The Quest to tell the stories of the human journey behind trailblazers such as The Chainsmokers, Mark Cuban, Steve Huffman and Bryce Hall.

Here are some of Brent’s thoughts on podcasting, no-code and founder journeys. You can find Brent on LinkedIn and Twitter.


Jeremy Au: (00:30)

Hey to you again.


Brent Liang: (00:32)

Good to see you, Jeremy.


Jeremy Au: (00:34)

I'm so excited to share your journey, all the up, down, sideways, part of life. I'll be a fun chat.


Brent Liang: (00:41)

Yeah, 100%.


Jeremy Au: (00:43)

The big question on everybody's mind is, who are you?


Brent Liang: (00:46)

I'm Brent Liang. I'm a 23 year old. I'm a law school dropout. I'm currently working as the co-founder and executive producer on The Quest. Which is a podcast project with Justin Kan, the co-founder of Twitch. Before that, I founded three different companies and I'm also a recording artist and I try to paint pictures in my free time. I guess that's a bit of a rundown about who I am.


Jeremy Au: (01:11)

Let's walk through the beginning. Where does the beginning of your professional journey begin and kind of walk us through that chronologically to where you are today?


Brent Liang: (01:20)

Yeah, for sure. I think the start of my professional journey was probably after I finished high school and starting my first year in university. I chose to do law because I wanted to get better at English. I thought going through six year of law school would help me be able to speak English and use the language in this really great way. Because I lived in China for 18 years, so Mandarin was what I've been speaking for 18 years pretty much. I wanted to be a lawyer. I think that's what I thought when I got into law school. But very quickly, I looked at some of the law firm partners and I had some internships and I was like, "I don't know if I want to be a lawyer." That would be the start of my professional journey, but I think I took a really quick turn after a year in. I built my mini podcast project in my first year of law school. It was actually about torts, which is a subject that we learned on civil wrongs.

For example, if you go out, if your car got jacked by someone, or if your bicycle got stolen by someone, that's a torts offense and you can take the person to court. I thought that stuff was interesting. I don't know why I thought that was interesting, but I tried to make a podcast out of it. Got a couple of friends, got some lecturers or tutors to come on board. I didn't know how to make anything, I didn't know how to do anything. I just basically watched a bunch of YouTube tutorials, learned how to use GarageBand, and I start to produce this mini podcast series. It went really well. I think starting from there, I was like, well, startups seems to be pretty interesting because we are also trying to figure out stuff, projects that you can build. Yeah, I think that's the start. Aspiring, I guess, law student disillusion about the world, and so I found myself in the deep building startups.


Jeremy Au: (03:06)

Awesome. What was it like building your first set of startups?


Brent Liang: (03:08)

That's a long story. I mean, second year after building my mini podcast project, I launched a project I didn't know what to do with it. I think we got to a couple K listens/views on SoundCloud, but it left there. I actually didn't know what a startup means at the time, so I enrolled in this competition called LawWithoutWalls. Which was this international conference program that brings together lawyers, law students, VCs to build what they call projects of worth. It's like a semi startup kind of idea. Our first startup was called Kite. It was in the legal tech industry. The idea was we're able to build something kind of tech tools for Aboriginal and Torres Strait Islanders. When some of the juvenile offenders, when they're sitting in bail, we would be able to assist, connect them with a community network and help them get better support system instead of them getting into trouble when they're sitting inside.

That was what we got assigned as a project of worth. I mean, I saw it as a startup, it turned out that it was slightly different and when you're going for a competition. I think it was four to five months of just researching and talking to people. It was very difficult for us because it's a very different, I guess, segment of audience that we're interacting. To an extent it's like, we didn't know our customers that well. It's not like you're building a startup, let's say, delivering food or I don't even know, like e-commerce where you can actually take an Uber and chat to your customers or pick up a phone and call them. For us, our end audience are very much like a whole other segment of society that would have to consciously reach out and chat to, and it's very difficult. We spent a lot of time trying to do all of that, outreach interviews. I think we did 40, 60 interviews before we actually started building our thing. But even with all of that ...

I mean, I had amazing mentors who were able to guide me through every single step of the journey, but I was just a terrible founder back then. I didn't know any better. I didn't know how to build a product. I didn't know what it really means to acquire customers. I thought you can get by without having a customer. I don't know how that thought crossed my mind, but I think I was very stubborn in thinking that startups are pretty much just about building things. That's not it. You're solving problems, you're not building things. Towards the second half of the year, we started seeing problems. We had a brief idea for an MVP, but we weren't able to really onboard any customers. At the same time, all of the problems that I mentioned about not being able to chat to our customers closely started to show up. So we had some miscommunication issues. I had a lot of workload on my plate and I was really stressed out by it.

I got a team of volunteers and it turned out to be not a very smart choice because the work that I was doing were just work for the sake of it. You actually spend more time managing people instead of just getting those work done. I was not a very effective leader back then and towards the end of the year or something, we had this miscommunication with a really big stakeholder. Which was a court and the whole thing just boiled over, it got really ugly where there were lots of emails that were threatening or sent. It got me to a place where I was really conflicted about whether I should pursue the startup or not, because I felt like pursuing it would mean to tackle one of the things head-on. Actually, it would result in harm to the community that we're trying to serve because we weren't able to navigate those landscapes as skillfully. If we shut it down, obviously that's something I've worked on for almost a year, I felt terrible and the team feels terrible as well.

So sort of like you're stuck between a rock and a hard place. Eventually, we did shut it down after a year. There were those days, I think we talked about this earlier before coming onto the show, but there were days where I felt really bad that I would wake up not having the strength physically, mentally to even check the email inbox. I would go out, take a walk, take a run, come back, do my pushups, go for a shower, and then click open the email inbox. But even then, you still get those mini spikes of anxiety. That's something that tends to be typical for lawyers. But I think for me, it happened at a much younger age. So I kind of felt what it was like to be controlled or to have your startup turn into something that feels like a monster. It feels like a really, really bad day job. I was only aware that later on that, that wasn't supposed to be how it feels. But I thought at the time that, when you talk about startup hustle, that's how it feels.

I'm glad that we closed it after a year though. I think that was a smart choice to make, and I think I made a lot of really good personal human connections throughout that whole experience. I think it really grounded me at such a young age thinking I could do anything in the world. Whereas building a startup is actually quite tough, you have to solve a real problem. It doesn't matter what you profess to be good at.


Jeremy Au: (08:06)

Wow. I mean, that's one heck of a journey. I think you said a couple of really interesting things, which is, being a first time founder is hard. That's one. Then two, it almost sounds like you've gotten the self-awareness of what was normal and then what was abnormal or difficult only after the first time as well. Which is, I think a very common journey for so many first time founders. It's like, they know they're struggling. Well, they are struggling. They don't know they're struggling. They think struggling is normal. Then when they're out of it, they're like, "Wait a moment, it's different. The approach I could taken could've been different." I personally share that thing. I mean, there were so many times in my past two companies where, I actually couldn't do the email either and I would just give my phone to my wife or my sister and I'd just be like, "Can you just read the email to me?" Because I'm like, "Okay."


Brent Liang: (08:57)

I wish I could do that. I don't think my parents have read my emails, but maybe I should have tried my brother.


Jeremy Au: (09:03)

You could have tried that. There's a handy trick is, because you want to read it, but you're like, I'll just give it to my wife and it's like, "Okay. I'm supposed to read this an hour ago, so it's not too bad, but I know I'm procrastinating. If you can read it to me and just give me the gist of it and then I'll just tell you what I'm going to reply." That's good enough because I'm worried about the tone, I'm worried about all the stuff. When someone else is summarizing it for me later, I'm like, "Okay, I know what I need to say." But I can ... I think one of my realizations only after my first company was, I really need to move a lot of tough decisions into a verbal meeting. It was just like, there's just way to make tough emails that were just, I felt it was impossible to solve over the email.

Actually, it was pretty much impossible to solve over email because personal issue, it's not a logic or a tax issue. So I was procrastinating and I was making things worse. Whereas, I need to move that into the personal domain. It's a personal decision, you got to make into a personal domain. All that stuff, I only realized after my first company. It was just like, "Oh man, I wish I knew that earlier."


Brent Liang: (10:02)

Your first company always teaches you so much. In a way it's almost like it's great if it's a failure because you learn a lot more. I think that sort of steepness of the learning curve is hard to be replicated if you do it for your second or third, because you've got a lot to lose. So you wouldn't be able to take on those learnings as quickly.


Jeremy Au: (10:21)

Yeah, I totally agree. I mean, I think there's this classic thing where a startup is supposed to be a hockey shape in terms of growth. Then humans don't have hockey shape in terms of learning curve. They're mostly linear or flat even. I mean, I always tell people, I was like, when I was in the middle school, is every year I did one year of math. So year one, you got one year of math. Year two, you did your second year of math. Year three, you did another one year of math. Yeah four, you did another one year of math. But if you are supposed to be succeeding as a startup, is year one you do one year of math. Year two, you do two years of math. Year three, you do four years of math and then year four, you do eight years of math. But nobody does that.

We would be, if we were teachers and trying to teach your kids, they would be like, as principals or teachers would be like, "This is a messed up way to teach kids because all of them are going to break by year two or year three." I think one thing you said that was very true, which was that if you fail, at least you may not have learned about the business itself, but at least you learn about your own rate of learning. Which is actually much more important because whatever you do in your next startup, the only thing you carry over is yourself. Right?


Brent Liang: (11:29)

Exactly. Now, that's a good quote.


Jeremy Au: (11:32)

What did you carry over to your second venture?


Brent Liang: (11:35)

What I made sure to do in my second venture was, we wanted to start thinking about customers from day one. We wanted to have this really clear vision about who's going to be paying from day one. I tried to make sure that we get to our product piece a lot sooner than what I would otherwise typically do. A bit of backstory about the second startup. I was able to meet someone really fortunate when I was in Sydney, and this person came from Myanmar and she was about to embark on some social influencer work. She wanted to make content. She wanted to be a content creator. So I had the opportunity to travel to Myanmar where I was able to understand the market conditions a lot more, talk to people, get to know people. We built this business that's of her personal brand. Which actually went really well and she was able to get to 1 million followers on Facebook relatively quickly. We built this business that's basically like a ... The vision for it was we wanted to be the biggest MOOC from Myanmar.

I think one thing that we nailed down really well, which helped us get to product-market fit was that we've had this format of influencer led soft skill training. The classes aren't just taught by instructors, they're taught of people who have a brand in the country. One thing about Myanmar is, whenever you wanted to sell something, because they're services, it's much better if you're able to tie it with someone that people actually trust. That worked very well with that in Myanmar. I don't know if you can replicate that to other countries in Asia, but at the very least, what we know is it would really work in Myanmar. We were selling courses on soft skills on basically things that you wouldn't be able to learn that much in the university. We weren't teaching any physics courses or anything that's hard science. It was more like language, business skills, stuff that's actually practical and useful for folks. Because a lot of them actually haven't gone to university and we don't want to take that ...

We don't want to be sort of this alternative education program for them. It's too much risk for us. But we did all of those courses and it worked really well. I think one of the reasons why we got there quickly, it was like I said, when you have an influencer, in a way your customer acquisition channel is a lot more smooth. A lot of people who came through or converted via my co-founders brand. We were able to charge for the classes relatively quickly. I think one of the important moments for me was I was always thinking that this has to be a MOOC website, so we've got to build something. So I got to learn how to code. I was learning Python for a month. I didn't even know why I was learning Python to put in the website. But anyways, at one point I was like, "You don't have to do all of that." Everyone was on Facebook in Myanmar, so why can't we build something, leveraging the tool set that we've got from Facebook? We took a few days and we launched something.

It's super simple. Once someone wanted to pay for a course, they would just transfer the money into our bank account and then they would do a screenshot, and then they will send that screenshot to us. Then once we check that, we'll just add them into a little secret Facebook group and then we'd push all of the videos from there. It made so much sense if you think about it, but it's like, we can do that in a week and get the whole business up and running. It's probably not going to be able to scale very well once we hit 40, 500 K or something. That's actually proven to be a wrong assumption. It worked well once we hit that volume as well. But we launched it and we just basically ... That was our MVP and we never really upgraded our MVP. We just kept it running for almost two years straight and we got to 40 K MRR in a year.

The one mil ARR by the by a year and a half. We scaled our team to 15, 20 people. I got to give credits to my co-founder here because I was actually ... I came back to Sydney. I was in Myanmar during my university breaks, and so I came back to Sydney for most of the time doing my studies. She made everything happen on the ground, and she's amazing. I'm really glad of how much progress we were able to make it such a short period of time. What that meant for me, I think, just to answer your question in terms of new learnings and stuff, is, first of all, a set of problems that you deal with as a founder, starting out to find product-market fit is very different from the problems that you face after you've found product-market fit. I think one of the things that I struggled with earlier on was building, talking to customers and building the thing that they actually want. It's like an art.

You have to really remove your ego from the equation and literally just take on this role of a designer. You've got to design whatever makes sense for them even if it's not something that sounds really sexy for yourself. That was the times that I had to get over myself before EMF. But after that, after we started to get revenue and you started to have team members come on and stuff, for me, one of the bigger challenges was hiring. I had no idea what it looks like for people that we'd bring into the team. Designers, no idea how to hire them. Coders, developers, no idea. I would read a lot of articles, I think culture fit. What does that mean? Zoom calls. If I chat to them, I like them, great, they're in. Sometimes they'd fail miserably. They don't know how to even put up a simple design work or they don't know how to do things at the spec that I want. Which I didn't really communicate very well to them before. A lot of those problems started to surface up.

Then when it comes to team, I think that 80%, 90% of time came from communication. We weren't able to do our communication well. So lots of inefficient meetings, lots of folks getting into almost mini arguments with stuff that wasn't transparent and just emotions and resentment that came from not being able to express things very well. I think one of the things that I realized was when you have those problems in your startup, it doesn't make any sense to blame anyone because all of that just manifests from the founder. It's almost like the startup is a reflection of yourself. If you're able to build ... If you're not comfortable with all hands meetings, then you will tend to run less of those. Then when you'd run less of those, people will feel like there's not as much of a need to communicate. Or if they work on a project, it's not as not really worth it to make sure everyone else understands. In a way, you're setting that culture and that manifests from your preference to not do those meetings too often.

Which the root cause for that could be that you just need to train up yourself to have more confidence. Little things like that, always coming back to thinking, "What did I do to make it happen? Okay, here's my character flaw." It's like a mirror. You're holding on to a mirror and it shows all of the character flaws in you. So I learned a lot from that and I think it really takes almost your co-founder or other people, mentors to make you aware of those things and to give you actionable steps about what you can do to improve. So that was one of my biggest learnings for my second startup, managing a team and making sure that the team has crystal clear communication. I don't think I did a really good job at that at the point where I left, but I feel like that was the growth that I experienced the most I mean, in terms of just how I see myself grow as a founder.


Jeremy Au: (18:44)

I just want to underscore to the audience how important what you just said was, about the company and the startup as a reflection of the founder. When there are problems at a startup, it is often a manifestation of not necessarily problems of you, but who you are and how have you chosen to conduct your actions. I think that's a super underrated comment because it's a very tough thing to say. I mean, we always hang out with other the founders and the founders are like ... I remember this friend and this guy was like, "I don't understand why everyone's selling so hard. We need better marketing, we need ... Everyone is too salesy internally." I looked at him and he's the most salesy guy that I know and I'm just like, "Well ..." As a friend, it was an awkward thing to say. Then you're like, because he's doesn't trust your friendship and relationship and then say, "Look, you came from a sales background, you'll building a company in sales. You're hiring lots of sales reps. Yeah, everyone's going to be more salesy.

Now what you're saying is you want to round out the team." But it's a valid acknowledgement which is, you can't build a sales company with just sales. You have to do other stuff like top leadership, marketing, people leadership, all kinds of different things, and then you're a part of it. It's not a bad thing, but we have just to get intentional about it. But it's not a bad thing, it's just we build the things that we're most comfortable with. I just want to say how underrated a comment what you just said was. I think so many founders have that struggle because they build something and they're getting a product-market fit and then suddenly it works. Suddenly an investor comes in and then they're growing or whatever it is, and then they're like, these are all these terrible things happening. It's a tough conversation.


Brent Liang: (20:25)

It was like stuff is just breaking every day and there's always a problem that's going on. I think it's really funny because for us, we never really raised a round, if that makes sense. I think it's really fortunate that we didn't have to do any of that because I think a lot of times people are more concerned about raising money than getting their product to be working. Which is a very big myth in this whole industry. I think for us to bootstrap and go all the way to 1 million ARR, that's something that I'm really proud of. But at the same time, it does feel like there's not much of a support network. I'm pretty sure if we've got more angels let's say sitting on our board, we can basically call out for support. We don't really have any for that to happen. For us, it was just tackling it head on and be okay with things breaking every day. I think a lot of founders will say that even when you start getting revenue, that's just the start of a new journey and things will still feel shitty.

I actually tend to disagree. I think things feel shitty, but you know you're safe, and that's a really good feeling. When you get money coming in every single week, when you get customers paying and they're happy in some way, you're dealing with problems, but then it doesn't really ... It's not existential. I think pre-launch, before you get to PMF, things are pretty serious. If something is not working, if you launch an experiment and it doesn't seem to work, that would get to me and I'll be like, "Okay, I need to work 10 times harder. I don't know when this is going to work. I don't know when this is going to hit that mark." But once you hit that, once you get to PMF, it's about how fast you can go to grow. That challenge feels a lot more, I think, urgent, but less intense, if that makes sense.


Jeremy Au: (22:04)

Yeah, that makes total sense. I think founders say it's more difficult because they don't really have a language to say, this is new. You know what I'm saying? It's not more difficult because you and I both know it's way more difficult to have no money and just be burning all your savings while trying to cut your expenses to zero. That's very hard and I think so many founders sometimes use the wrong language to say raising a seed round or raising a Series A it's hard. Don't get me wrong, it's hard, but it's not hard because it's hard. It's hard because it's new. Sometimes the language matters so much. It is like the first dollar in, the first customers, they're not hard, they're happy, they gave you money. then you're like, "You're giving me way more value than I thought I would. Because your customer support,"

I remember I was buying some service and I managed to break their service. I knew him from a while ago as a friend. I messaged him and I said, "Hey, I signed on too many users for this case and I think I broke your product." Then he's like, he personally, the founder personally responded to me and said, "Okay, let me fix it." I'm thinking to myself, "You know what, I'm paying what, five, 10 bucks a month? I'm totally getting my bang for the buck. I'm getting the founder. A former YC guy to fix my customer support for me, my problem for me. This is great. I think it's so much of a framing thing. It's like customers are happy to throw money at you and then founders are like, "This is hard." When they should just be like, "This is new and it's uncomfortable."


Brent Liang: (23:35)

I like that reframing. I think that's very helpful.


Jeremy Au: (23:37)

What was new for you? I mean, obviously, well, I think what's also not new not only was the industry, but also the geographies as well. Which is just something I've noticed it's very special about you so far is, it feels like you've been quite ambidextrous industry and you've also been very ambidextrous in terms of geography. I'm just kind of curious about how you think about that.


Brent Liang: (23:57)

Yeah, for sure. I don't know if I qualify as a Gen Z, probably not. A tiny bit. I missed that train. But I think I'm lucky to be born in an age where I actually think geography doesn't matter as much. I was born in New Zealand. I moved to China when I was six months old. Technically, I'm a Kiwi, but I'm actually not. Then technically I'm Chinese, but I don't have a passport or an ID. Then when we build our business in Australia, everyone will look at me as an Australian and that's not technically true as well. In a way, it's almost like I was brought up in a world where those labels just don't tend to apply as much to me. I mean, it obviously resulted in its own problems where I think I moved to five, six different high schools growing up. Being able to form friendships or build relationships quickly with people was a life skill that I had to learn, otherwise I just don't any longterm sort of friend or attachments because I just move around too much.

But when you're able to realize all of that, it makes you feel that it doesn't really matter where you've been brought up and stuff. The two co-founders for my first startup, they were from the US and South Africa. Remote work was something that the LawWithoutWalls program has been pushing since its beginning. It's so innovative, but we got used to basically that whole work style before all this stuff with COVID happened. The whole year we were working just purely via Google Hangout calls and I thought that was a natural way of working because I got into obviously my second year of university. I thought that was the norm. When I got used to it, it doesn't really matter if my second co-founder lived in Myanmar and we chatted over FaceTime. It didn't really matter that for my first startup, we actually traveled to UK and we came to the US, met with Bill Clinton. All of that stuff was like, wherever opportunities are, if we can get a ticket, let's say to go there to talk to people who might be useful for our company, let's do that.

I think with COVID, everyone is seeing that happen in live action. I got onto this current project with Justin Kan when we have no connection with each other whatsoever. I'm just a random kid in Australia. He's living somewhere in the States and we wouldn't be able to even know each other for our entire lives. But once you have the right channel on the internet and you're able to trust someone else and you're able to build something with them and communicate frequently, anything could happen. I think you can build a startup, you can build whatever. I even know you can probably build a lot of other stuff as well. You can probably start a TV show or something. Like you would do this podcast. This is crazy. This is a really good example. I don't know you, but we met through OnDeck and now we're doing a podcast together. I feel like I'm having a conversation that's so authentic and deep. It's almost like I'm talking to someone that I've known for a couple of years.

So I think that's something that we're seeing a lot more in this new age. We just got to get used to it. I don't even think about geographies. Maybe some investors will be concerned possibly with some of that stuff, but for me, it's about the person, it's about where we can make the product work, and it's about whether the market is good or not.


Jeremy Au: (27:14)

Yeah. That makes a lot of sense. I'm sure the question that everybody is thinking to themselves, how did you startup one, startup two, startup three, and now you're with Justin Kan. I mean, this guy has got founders talking to him, or try to email him out the wazoo. He's YC. My last co-founder Tatyana and I, we would follow him on Snapchat and we would laugh at him driving his ATV up to his wedding in California. I've also personally met him a few times, actually at the last company, Atrium Services. I've worked with other executives that have reported to him. But I was just kind of curious, that's very different from you being a client to pitching or consuming to you working with him. How did you do that from the middle of nowhere, I guess, versus the center of the universe being America?


Brent Liang: (28:02)

Let me just quickly run through how I got there. I think I want to talk a bit about my first startup, because that's what led me to this path and more of a connection with the US as well. But basically when I came, a year or two after we set up Chance Myanmar, the Myanmar business and we were making a little revenue, I thought I couldn't see myself doing this for the rest of my life. I took a step back, I became more of an advisor in the company and I wanted to build something that's a lot more scalable, something that's on a global level like YC, Ready, something that's going to change the world. I think that's what young kids typically think about when they're trying to go big. I wanted to solve the problem like I said earlier with me hiring. I saw a lot of my founder friends who were quite young who were able to raise lots of money who had trouble with hiring. So we wanted to build this platform that's able to distribute these hiring challenges for them.

If you wanted to bring on a designer, we would co-create some kind of design challenges that would basically let you test for what good looks like. You would send that challenge to a designer before you wanted to bring them into the team. They would finish the challenge and us a platform, we would rate the challenge in some way via our algorithm. So that gives you a pointer or an indicator about how good the person is before you have them come in. We built that web for this competition called the Hult Prize, which was a pitching competition. We were invited to go to pitch in Dubai and we won that round. We got to the UK, stayed for two months in a castle, we built the business. Then we went to the US, met with Bill Clinton pitched, but didn't really get the $1 million coming through. Then I lived in Silicon Valley for two months. I think when I was couch-surfing through the US, I had no money on me at the time, and I stayed with really good friends in a house for two months.

That whole period just changed my perspective. It changed my perspective about what's possible. When I was in the US in Silicon Valley, I thought I was going to leave after a couple of weeks. I was like, "This place has some of the best, most brilliant people in venture, in startups around the world. I need to meet them. I don't know how I'm going to get to them, but I need to meet them. Otherwise, I'm just going to take a fight all the way back to Australia in 20 plus hours." That sounds pretty bad. So I was like, "What can I do to meet them?" I was stuck. I was trying to find out emails and I sent a bunch of them. I heard from some, I didn't really hear from others and I was like, "I don't know how to do it." But then one day I talked to one of my friends and they were just like, "Just take an Uber. Show up at their house and talk to them." I was like, "What? I cannot imagine how you would even say that."

But then I thought about it. I was like, if I can somehow manufacture this opportunity to meet them or to make an impression, there's nothing wrong with that. So I actually did that. I would draft handwritten notes about what I want to get from each conversation and I would put that note in an envelope and I would go to some of those VC's residences. Which I was able to find out by actually using one of my old law firms credentials and check their SEC filings, whatever. Then I'll go there, try to see if there's any signs outside that says no trespass, whatever. I would pass the note underneath the door. Every time I did that, I would get the conversation coming through. It's so funny, but when I meet them in person, they'll be like, "I'm framing that note in my house. I'm so glad that you did that and let's chat."

It's funny because we weren't at the level where we're able to raise, a lot of those conversations didn't really materialize into let's say a Series A investor or something. But just being able to do that makes me understand that there's no need to glorify someone and say, you're not going to be able to meet them up until you get an intro. You don't have to wait for the intro to happen. If you just go meet them, if you take an initiative and just do a bunch of those things, things will come your way. When I came back to Australia, I was working on our startup for almost the whole year, got my personal burning rates to zero. I was having ramen noodles every day. Then towards the end of the year, we had our first customer come on board. Just in that one week I was on the server called ... A shout out to Gen Z Mafia, it's one of the best servers in the world out there. Justin obviously he sent a message saying that he needs help with his podcast and this upcoming book and he wants someone to basically help out with things.

I thought that's a really good part-time job opportunity. I was like, "I can probably keep things going. With a bit of money from here I can fund my startup and whatever." So I DMed him, sent him all of my design samples with 30 plus files. Every single message got sent as an individual message. Which was crazy because I was just spamming him out of nowhere. This random kid from Australia spamming him with all of those graphics. Later, I knew that that's actually what he ... He wasn't looking for any of that. He was looking for people who was much better at producing things and I was sending graphic design or whatever. But halfway through, like 50 messages in, he was like, "I love it." I was like, "Oh shit, let me keep sending." I sent another 15 or something and then he was like, "Let's chat in two hours." So I was so nervous I called everyone that I knew. I called my co-founder. I talked to my parents. I tried to raft to get myself ready and all that.

I got onto a call. He was sitting across the screen. He was like this Asian Jesus guy. I was a big follower of Justin for a long time as well. So seeing him in all of that majestic hair flowing down, that was surreal. I talked to him and the one thing that I realized, the first couple of moments into the conversation was just how vulnerable he was with me. He talked to me about all of the things that he's been thinking to do and he talked to me about all the things that he's not sure about. Like he wasn't sure about let's say if we can make this podcast go big. He wasn't sure about what kind of help he actually needs. He wasn't sure about what kind of strategy in terms of promotion we would need. So he was asking me for help. I think when you come to someone for help, it's a lot easier for the other person to pitch in and ... It kind of destressed me and it made me a lot easier to engage with him as a person.

I think that first chat went quite well. I drafted a plan or something and sent it to him. A week later, I came in as the co-founder and executive producer for the podcast. One of the visions that I pitched him was, I see a lot of things that are special with Justin and with his podcast. I think it's just a matter of time that we get to be bigger than Joe Rogan and moreover that's not it. We're not even competing in the same arena. We are building a cultural product, a media company, that's going to go beyond just an audio service. It's something that it could be one of the most exciting things cultural product like audio rising that's going to be able to be seen as the most exciting projects for founders and creators worldwide. Justin is one of those only people in the world where he can bring people like Michael Seibel and then have a chat with Chainsmokers the next day. He has the ability to bridge industries like that, and I think that's super special. I pitched him all those visions and he was on board from day one.

We also wanted to try something different where we're trying this whole concept of building a community around the podcast. Which since has worked out very, very well. That's how it went. A week after I came in, I had a chat with my co-founder again and we were like, "Okay, well, it doesn't really make much sense if we wanted to keep both things going because I don't want to fail at either of them." So we actually shut the startup down, we transitioned into a ... We actually gave our product piece to another startup who were two of my friends, really good founders. Nothing that we've build has been wasted and it felt kind of great to say that. Just basically since then I've been dedicating full-time to growing the podcast and all of the other personal brand initiatives for Justin.


Jeremy Au: (35:52)

Wow. What an amazing ... I don't know what's the word. Adventure and so brave. I mean, a lot of bravery there at each stage and each day to do what you just had to do. I think the thing that jumped out to me was the part where you always push yourself to do something crazy. I'm just saying, that's like, I think everybody knows they got to work hard and people do work hard. That's going to give you good results. But sometimes you have to do some crazy shit. Either you get zero from the market, sometimes you get negative repercussions, but most of the time you get zero. But sometimes when it does work, it works. It's interesting where, I love the part where you're like, "Yeah. Worst case scenario, they would just ignore the letter under the door." Then the basket scenario is they actually pick it up. The worst case scenario of direct messaging Justin was, he would just ignore you or tell you it's bad.


Brent Liang: (36:51)

I wasn't losing anything. It wasn't on my board. He wasn't someone that we wanted to bring into our company or anything. So even if I don't get a reply, it's like, "Okay, well, that's not going to ... I can still go about my day and do whatever I do every day." If anything came through, it would just sort of change my life in a way, and it happened. I think that's super important. Actually one of the things that we used to do at our third startup was, we would set aside this time called moonshots, and every day we'd try to spend 20% of the time. Which typically it rounds up to an hour just doing completely impossible things. We would email Elon Musk, we would email, let's say Sam Altman saying, "Can we put in a Zoom call?" Email the founders of Canva, who's an Australian and who she's killing it, Melanie, and saying, "Can we go and grab coffee?" Things like that. We never really got any proper response. I mean, there's a lot of interesting people that came through, but we just kept doing it.

I think it cultivating this habit where when we saw something ... It got me to Thiel Fellowship interviews, that kind of level. I think that was really great because if we didn't have that habit, that kind of mindset, none of this stuff would actually happen. We probably wouldn't even get to our first customer. The thing about moonshots is, whatever you do, if you do it long enough, you're always going to land at a spot that's higher than what you would originally be. You just basically heightens up your trajectory, and I think it's super important. I kind of hope that, that's a personal development goal for people as well. Just every day, try to do something that's outside of your comfort zone. That's a very, very, very ... There's a small percentage of it succeeding, but if it does, it's going to just flip your life over. I think that's a very healthy way of just trying to make sure that you're going somewhere every day.


Jeremy Au: (38:32)

Yeah. I love the framing that you use the word moonshots. I never thought of it that way. It's such a good way to frame the negative way of saying it which is doing something crazy. Well, the way you frame it is a ... I think crazy is still neutral in the startup world. I think doing something I think negative would be like, people say that you're doing something dumb or it's not worth your time. I think that's a negative frame. But I think moonshots makes it have a positive frame to be like ... I like it actually. I think it's a good way and I'm going to have to write it down on my own vocab. Which is you know not every day, but I think every week I could do maybe a moonshot. I'd be like, today, I'll have the raspberry with Nutella ice cream. Maybe that'll still be my moonshot.


Brent Liang: (39:13)

That's not what I meant, but I'll take that.


Jeremy Au: (39:16)

I want to go double click on something that you said that was interesting. Which was the realization that this demigod, this Asian Jesus was also human and asking you for help and being open and vulnerable with you. How did it feel going through that? Were you surprised? Were you disappointed? More accepting? Did you feel all those things? What is it like to feel the crash of the illusion, the stage and the reality of a person on a video call with you?


Brent Liang: (39:45)

I think that's a really great question. That's something I kept asking myself as well because I try to observe how things have changed and how I've felt the dynamic between me and Justin to be like. I think one of the things that I can definitely say, and you can see this a lot in The Quest, it's one of the central messages we wanted to drive forward in The Quest. People are people. Eventually when you talk about some of those fundamental issues that we all go through getting our personal wellness done right, or trying to go after one of our goals or trying to go after something that you really want to do, and for that you have to crawl through miles of shit, everyone is connected on some level. All of the trouble that results from people not being able to connect is due to miscommunication and people not willing to share that because of the perceived threats that they would lose some kind of personal image in someone else's eye.

I think what Justin does really well is ... I mean, there's a side of him that I think is a really forceful executive and that's something that he was very open about as well. There are aspects of that that made, I think all of his companies successful, that pushed me to be the best version that I am and that pushed the project and all of the stuff that I was working on to ... We were hitting those targets and numbers left and right. But there's also a very human side of him and I think that's something that I was really lucky to get to see. He made it come across super clearly from our first meeting. It was literally from the first thing that he said, I felt he was just very vulnerable and that he needs help with some of this stuff. He actually doesn't need that much help, but he made me feel that he is super welcoming. It's so funny, ever since I came onto the podcast, we were in ground zero. So we had to set up a lot of things up.

So I was texting Justin almost every single day. Every single day, like 50 plus text messages. I wasn't even thinking about it, but a week later I was like, "Yo, am I texting the co-founder of Twitch 50 plus messages every single day? Who else in the world does that? Should I be paying money for this?" It's just crazy. Sometimes he would just call me, FaceTime me out of nowhere and I was super stoked whenever that happened. But then it got to a point where I was like, yeah, he wasn't faking any of this stuff and he wasn't trying to do me a favor or anything as well. We were just two people who were trying to build something great and trying to make something happen, and in that process, get to know each other better. Get to know each other's goals better, all of our problems in a way as well. It's literally like a co-founder relationship. I mean, it's one of the best I've ever had. I think when we built up that trust, we would set up weekly sync calls.

But then when he would get busy and we wouldn't talk for a while, and I wouldn't feel anything. I wouldn't be like, "Okay, I don't know, we haven't got a contract down or something. Should I be worried about being dropped from all of this? Should I find another job as a backup?" I never worried about any of that, because the trust was so strong and I knew that fundamentally we care about each other as a person. I cannot stress about how important it is or what kind of skills you have to get to build that kind of bond with someone who's 10, 20 years younger than you. Justin is at an age where he could probably be my dad. I think just being able to forge that kind of connection with someone who's Gen Z ... A lot of times we argue a lot. There are things that I wanted to do that he doesn't agree with. There are things that he ... When I proposed something, he would poke holes in my ideas. If I was the me two, three years ago, I would get very offended or I might suffer.

I might be defensive. With all of these, with that fundamental piece of trust that's in place, a lot of this stuff becomes productive. When it's productive, it feels good. Even if our ideas sort of conflict and even if we argue, even if we do all of that, like I said, it's just really healthy. I can see that his ability to do that obviously it came through lots of trial and error and he's had his fair share of success and let's say failures in his professional career. But I think that ability to connect with people is what made Justin Kan very special and one of the best mentor/co-founders/celebrities I've got to know.


Jeremy Au: (44:00)

That's amazing. It's interesting because you really see the evolution of your relationship from stranger, to spamming, to kind of building out together, to storming the norms and where you are today. Obviously the journey is only just getting started. I think you said something really special, which was you're kind of implying it, it's like, you're young, but you're not inexperienced. You just experienced in a different way. Does it make sense? You're younger, but you're not young. I mean, you're not in diapers or anything. You're younger, but that's a strength of its own. Because there's energy to get stuff done, openness. Media is getting consumed by Gen Z, even though we're not Gen Z, but things are moving fast. We've got to be aware of the mediums moving fast. I think a lot of people self-disqualify themselves as founders or co-founders and they're like, "I can't do this or that because I'm too young."

I'm like, well, it's less about whether you're too young. It's really about how your experience has brought you to it. If you're young and you're experienced enough to tackle the problem, maybe because some people are like, "Yeah, my family used to do business in agriculture and so I know all about agriculture." I'm like, "Yeah, you know more about agriculture than someone 10 years your senior." Heck, I could be 20 years your senior and you probably know more about agriculture than I do. Because I've done zero work and I just consume vegetables. It doesn't mean I know anything about vegetables, but you grew up living, breathing on a farm, on a plantation. I like what you said, I think you kind of started sharing a little bit about the strengths you bring to the team on the conversations you have. For me, I guess the question I have is just like, how do you stay on top of all this stuff? How do you learn? Because like it or not, even though this is not necessarily a startup startup, it's still, I think ...

I definitely feel each company you're doing is again, slightly related each other in terms of the individual skills, but totally different in terms of industry, in legal, MOOC, hiring, and now podcasts. That's really four different industries from a pen and paper approach. The only constant is yourself and so you're learning fast and everything. In what ways are you learning fast and in what ways do you feel like you're learning slow or need to improve?


Brent Liang: (46:22)

I think I tend to learn very fast when I feel like I'm out of my depth, which is scary. That's something I'm actually trying to optimize and improve on. Because I think when you do something driven by fear, it might work very well, but it's not very sustainable. But if I look at all of the stuff that's happened in the past, when I felt like I was out of my depth and something needs to get done, and there's no one else that I can put onto that task where I need to own it, then I would learn crazily fast. For example, when I got put on to Justin's project, one of the first things that I had to do was, how do we 10 times our listeners in a month? I wanted to prove myself to him that we can do it in a month or two. But the only experience that I've ever had, my experience is primarily with building companies. I think I know a tiny bit about what that would involve.

But when it comes to building podcasts or following through any sort of media projects, like I said, the only thing that I've done was back in first year of law school when I made that mini podcasts and that wasn't very impressive. I didn't really follow through. But I felt like I was out of my depth and I was like, "I signed up for a job as a producer, but I don't know what the hell this job actually even requires and I don't know if I'm qualified." That's a very tough feeling to have, because I've kind of landed one of the best jobs in the world and I wasn't sure if I lived up to it. With that, it just stuck in my chest every single day, I would just consume articles, consume podcasts, consume all of the growth hack whatever medium articles out there, every single day. I tried to pass myself off to him, which I eventually realized wasn't the right way to do it, but I passed myself off to him as like I know what I'm doing.

I was like, "Let's try this. If it doesn't work, let's try it one more time." That made me learn very fast, but something that I've gotten, I think a lot better at right now, when it comes to those learnings is, being very transparent about what kind of help you need to learn in an industry. For example, I know at the moment I'm trying to get better at understanding new media. I sound like a boomer saying this, but I would understand, let's say how Twitter works or how LinkedIn and all of that platforms work because I was using those platforms since I was 18. But when it comes to TikTok and YouTube, those are the things that are quite new. For someone like me, I don't even feel like I've got a full understanding of it. I would try to get better at that stuff, but I wouldn't try to pretend like I'm an expert and then try to puddle crazily to get to that level. Like fake it until you make it. I don't think that's a very healthy way.

What I would instead do is figure out who in my friend circle is great with that stuff and just DM them and say, "I need help with this. I'm trying to get better at this. Can I learn from you? Can we get onto a call where you can tell me at the very least where I should be looking for learning resources and materials?" That's one of the things that I've been trying to do with OnDeck fellows, connecting and learning from each others strengths. I guess it ties back into being vulnerable with what you want as well. That just goes such a long way towards learning because we hack things. Yes, you might be able to learn very fast, but if you're set on the wrong direction, you actually learn a bunch of stuff that's not as useful that you have to later ... Almost later, they become legacy stuff. You're consuming a lot of get rich quick kind of tutorials, which might work in a moment but ultimately it doesn't really help you learn anything real.

If you're able to get an industry expert to point you in the right direction and if you're able to quickly sort through the materials, you can consume all of this stuff that's going to help you to get to the next checkpoint. That's a much more solid growth curve. If you talk to enough people, you can basically achieve the same level of growth without having to hack the whole process. I think that for me, has been a really great discovery. The conversations that I would have with Justin or anyone in the team right now would be like, "Okay, let's do this. I'm actually not an expert on how to do it, but here's how I'm going to be learning. I would appreciate it if you guys can point me in this direction or that direction." That's sort of the conversation that we try to have for everyone. Our writer might be asking in a conversation about how to monetize a Substack newsletter. Our designer might be asking that question to see how we can drive let's say impressions for native clips on TikTok.

Our production guy might be asking how we can do that for the best tech stack for recording the podcast. Everyone is vulnerable and asking for help, but then we all know what each other is working on. Then that becomes a much more symbiotic relationship, I think, among the whole team. I think that's better than just hacking things and making sure that people see me as someone who's capable, whereas everyone's super stressed beneath the surface.


Jeremy Au: (50:55)

Yeah. That's so true. It's a tough skill to learn to be honest. I mean, I think I, myself, I'm still learning that right now. Because everybody tells you that you're an expert on A or B or C and because you've achieved X or Y. It's like so many people are like, "You understand business because you went to Harvard Business School." I'm like, "What are you talking about? There's plenty of companies that have been totally screwed over by Harvard MBAs." Yes, all the top, big tech companies now are being run by MBAs now, but it's still a different thing. I think it's tough to be vulnerable while still working to share your expertise and be a leader because that's a tough Venn diagram to be part of. Be an expert, be a leader and be vulnerable. Then to be in the middle is probably the sweet spot where everybody loves you or everybody respects you and understands how to work with you. It's a moving target, like that spot is different this week and that spot is different next week.


Brent Liang: (51:55)

One of the things that I've found was I think more effective leaders that I've seen are folks who wouldn't really necessarily proclaim themselves as leaders. But if you asked anyone else in the team, their presence is so huge and it's so felt across the team. I remember when I was building my first startup, I cared very much about being a CEO and being on papers. If there's any press being done about our setup, I want to be on that page, in the picture because I felt like that was validation for all of my hard work, which was deserved. When we had a team, I would be very forceful in terms of exerting my leadership presence on the whole team. I would be like, "Let's set up weekly sync calls. Here's how I'm going to delegate. You're in charge of this, you're in charge of this and you report to me." All that. It was in retrospect, a lot of the things like carving up roles and responsibilities are the right things to do.

You can't function without setting up those expectations, but you can communicate all of that stuff in a much better way. I think leadership is 50% about communication. The other 50% is probably ... Not even ... No, maybe I think it's like 80% communication, to be honest. I think it's just about how you talk about stuff and how you communicate with each person on the team. Throughout the whole journey, going through startups and I think working with Justin Kan as well, it's like, I've learned to be ... Still, now, I don't consider myself to be a leader. I consider my role to be ... You know that guy that unclogs the toilets, that's how I consider myself to be. Whenever someone, if someone is put in charge of design or production and one day they can't do their work, they would have to ... There's stuff that's stuck in a toilet. What my job is, is I would just come in and just make sure that that whole channel is done, it's unstuck. I got to clean all of that stuff away so the whole thing is flowing.

Then whoever is doing that job can just manage the whole thing themselves. That's literally what I think of myself. It's a funny skill set that you have to learn. It's like problem solving. It's not like leadership per se. But I think that's what I'm trying to get a lot better at. Also a lot better at communicating what needs to be done and what we all want to get too as a team. Those kinds of skillsets, I think help me actually build much stronger teams without having to be at the forefront. If I disappear for a month, hopefully like a year, I feel like for my third startup or even for this current project, we've got such a great team that if that happens, nothing would change. I think if that's the sort of feeling that you get as a leader, it's very gratifying. When you rule as a leader, a very forceful leader, ultimately it sucks your life away and you can never detach yourself from the company. It's very scary.

Whereas if you are sort of more into transformational leadership, where you're building people to be the future leaders of whatever they're good at, eventually it's almost like you're hitting early retirement. I just feel like it's a much better way to make sure things gets done and people are actually excited about what they're doing.


Jeremy Au: (54:50)

Well, I love all you saying. I just got to push back on you here a little bit. I mean, you are a plumber where you're solving problems. I think you're selling yourself short a little bit here based on what we just discussed and what I know about you. There's at least two more identities I see you as I want to say out there. I mean, I think the first identity I see you is that you're definitely an explorer because you're doing moonshots, you're going to new geographies, you're going to new verticals. At minimum, on top of being a plumber, you're also an explorer and you're just finding out new things, learning when things are uncertain. That's one. The second thing I see, I think is really interesting is, I think you have a very strong editor view. I don't know if you want to call it editorial. I think obviously most people think of editors as these big, nasty, evil people who remove the voice of the artists, et cetera.

But I think the best editors are well beloved by authors and publishers, because it's a thought partner. It's a partnership. It's about figuring out the essence and writing the essence of that. I can definitely hear that editorial tone where you're able to summarize in many ways your own experience, but also the experience of the people that you've met along the way. I think you boiled down your first co-founder pretty well, actually. Then you boiled down your second co-founder actually pretty well as well. Also Justin as well, I think you actually captured the essence of Justin much more. Because if you asked me to describe Justin, I'll give you a bunch of anecdotes, but I wouldn't be giving you the essence of who he is as a person. I think you did a much better job in five minutes than I would have over a one hour dinner. I think you're more than the plumber, I think you're also an editor and a explorer.


Brent Liang: (56:37)

I appreciate it. I told myself after I failed in my first startup, I was like, "Communication is going to be one of my growth trajectories for the next five or 10 years." I want to be ... I watched one of the videos where Michael Seibel was speaking for YC, and that was actually my first time learning some of those YC stuff. He was such a great communicator. I was like, "I just want to speak like him." Honestly, when he says things, it's so succinct and it's so effective and he just doesn't waste any words on things. Later, I actually found out he was great, but all of the experienced startup founders are great in terms of communicating their business idea, their thesis, how the team is functioning, what kind of help they need. I think it's like a product of intentionally trying to work on this craft. I knew that I had to get there eventually one day or the other and that better to start early than late.

I think communication and well, being better at editing some of your stuff and being able to communicate things in a much more succinct way that get some of those ideas across, especially what about people, that's 100% of where me, myself, I try to grow in. I think getting back to your earlier point, I still think primarily the work that's being done for the podcast for everything else has been cranked out by people on my team. I think we've got really great editors. We've got really great designers on the team. What I think I might add qualify a bit to my earlier statement is, the majority of my job is plumbing, I'm unblocking them. But when there are new initiatives that needs to be taken, typically what happens is, everyone is so caught up in doing their work that you have to be the person who's let's say two steps ahead. For me, when everyone is ... If we moved on to let's say YouTube, we would spend a couple of weeks ... I mean, actually not that much time.

We would spend a couple of days to get our cover art stuff right and then we'd have the thumbnail set up. Before we ever launch, I'm already looking for the next thing. I'm thinking, "Okay, once this is done, what's going to be next." I would be looking into, let's say TikTok or some kind of growth hacks let's say integrated with some kind of newsletter or do we need partnerships? When everyone is trying to make that one thing to go well, I would start testing out this other channel. Then once ... It's quite scary when you put yourself in that position. Because when I go into this new channel, this new experiment, I have no support. I have to figure out what needs to happen. I have to figure out who we should talk to. What kind of emails should be sent? All of that. I think there's some sort of kind of skill set that I need to master in order to, first of all, spot where those opportunities are.

Then second, follow through on some of the earlier things that you can do, like build a basic framework of how things might work. Then once things start to work, once you have more people who you can dedicate, then it's like, "Okay, how do I onboard someone so they're able to do all of this stuff 10 times better than I can and basically not running into any troubles every day?" I feel like one of my jobs is, yes, I'm a plumber, but I'm almost popping between different pipelines. If that makes sense. It's figuring out what the new pipeline is, popping over and then try to explore for a bit. Get it working, put someone on it, and then go somewhere else. But if I stay in one place for too long, I feel like ... I would love to. Some of the stuff I actually like doing. Like community building, I love it. But if I stay in one place too long, that's doing a disservice to the whole team because my role is to not be stuck in one place for too long.

If I do that, we lose out on opportunities and experiments that we can run. But I think that's one of my learnings, I guess, as someone who's building teams. Using that plumber analogy is, yourself can get stuck in that place as well but you just got to keep moving around.


Jeremy Au: (01:14)

Yeah. I mean, I think the plumber is the base. I'm just saying, you've got the explorer and that huge editor point of view. Double click on something here. You mentioned this earlier. How old are you?


Brent Liang: (01:23)



Jeremy Au: (01:23)

Okay. When was your first startup? The one that failed. When you first founded it, how old were you?


Brent Liang: (01:30)

I think 18.


Jeremy Au: (01:31)

18. It's been effectively been what, five years?


Brent Liang: (01:37)

Five years, yep.


Jeremy Au: (01:38)

Five years. If you've managed to get from there from 18 to 23, can you imagine where you're going to be between 23 to 28? I know it's hard to think, but from the point of the listeners, I'm just pointing out these are ... I think you're speaking with the sophistication maturity of someone in their late 20s, even their early 30s, about how they see their role, about what things are there. I think there's a lot of exciting trajectory that you're going to have. I don't know if you see yourself, but as someone who is over the hill, headed towards the pastures as a 33 year old person, I see it. By comparison, I can tell you, by the age of 23, I had crashed off high school pretty much because my girlfriend passed away and so I was grieving. I was in the military for two years.

I joined undergrad when I was 21 and I graduated from university when I was 23. I was just entering, I guess my second job, I guess. You can tell that military is the first job. I don't think that you could have asked me to articulate a leadership philosophy. I mean, this is not a race or a competition to see who's wiser more mature at what age, but I just want to point out that.


Brent Liang: (01:01:52)

I'm sure there's tons of stuff that I need to learn. I have no idea how leaders were able to ... If you think about some of those other companies, when you're running 150, 160 people across the board, or if you have to balance up iterations from ... Let's say we had this interview with Emmett Shear the other week that we launched. Being able to manage a company like Twitch and manage, not just your employees, but expectation from the communities and stuff and your investors, that's a job that I think would be super hard. The same thing with politicians managing your electorate, managing people who are voting for you, who had expectations for you. I think those are much ... There are much greater leadership lessons out there. For me, I'm basically working with a group of friends that I like and we just make some clips here and there. There's not too much of a leadership philosophy that's involved.

I think five, 10 years later down, I wouldn't be at a level where I'm a complete, ever. It's just more about, how do I get to those places where I'm able to see and possibly learn from doing some of those more leadership oriented stuff. If you think about companies like Coca-Cola and then having offices around the world and being able to coordinate those kinds of activities from an HQ, that's some amazing skills involved. I don't even think that's something that you can learn from an MBA. It has to come from failures and repeated practice.


Jeremy Au: (01:03:19)

Yeah. I mean, as a friend, I would say, I think you put Coca-Cola on a pedestal. I mean, Coca-Cola was ... I think the biggest thing ... My favorite class when I was at Harvard MBA was I took a class in entrepreneurial history. I love history and I watch Extra Credits and all this history stuff, I read Wikipedia at night. I think I took this class entrepreneurial history. I think the part that was really interesting to me was just how every company was founded. Coca-Cola is a big conglomerate now and so as a fallback, it was founded by a founder and there were earlier employees that made it who it is today. Mitsubishi, the logo, he was a disgraced samurai whose house was on the rocks. He had to figure out a new route in a new Japan, modernizing Japan and he made it into Mitsubishi. Chanel was a person, a personality and someone who partied and she converted her name into a brand and a company ...

I don't know. I feel the movie, I think we fast forward to the ending too quick little bit. I think it kind of goes back to the first thing you ever said, which is the problems of the companies that have tough times are a reflection of the founder and the founding team. I'm pretty sure, I mean, as when this continues growing bigger and bigger, I think it's going to succeed and then people will be like, "How do you manage it?" You're just going to be like, "I just built it around the way I like to work." It's not just a shadow, but the upside is also going to be.


Brent Liang: (01:04:50)

Yeah. Well, that's the dream.


Jeremy Au: (01:04:51)

I think in the next five years you're going to build this out to something that's amazing and it's going to be built around the way that you like to build it. That's all. Everyone's going to be like, "Well, it's really difficult to lead this way." You're like, "No, this is the way I like to lead."


Brent Liang: (01:05:06)

Let's hope that happens. I'm trying to work hard every day to be as deserving of that dream, I think.


Jeremy Au: (01:05:11)

Yeah. I think, well, coming on time here, just coming to the last question here is just, there's a ton of struggling founders out there. I just recently met one and she was kind of having some tough times. But I feel like every day I meet another struggling founder reach us out. I mean, obviously it's one part technical kind of just, how do I solve X? Then one part is psychology, which is like, how do I do with this? It's like, this is not how to do this, and how do I do this? When you were in your first startup struggling, you're thinking about closing down, you're it's on the cards, and if you could travel back in a time machine, back to that person, I'm just kind of curious I guess what would you say? Where would you take the person? What would you show?


Brent Liang: (01:06:00)

Yeah. Well, jeez, that's a good question. In terms of things that I could do differently, I wish I closed it up earlier. I think I was way too attached to that founder's mentality of I have to see something through. I thought if I quit halfway, it means I wasn't dedicated enough as a founder and I wouldn't be able to achieve anything longterm in my life. That was wrong and I shouldn't do that. When the product wasn't working and we knew our conversations with customers was getting increasingly difficult, that's a really good sign that things won't be working out. I think I should have trusted my gut's feeling earlier to pull the cards out quicker and then move on to another thing quicker as well. But I think in terms of personal advice that I would give to myself back then, it would be, you don't have to reply to every email within five to 10 minutes after getting that, because people can see that you've seen it. Well, hopefully ... Now they can with Superhuman and stuff, but back then, I don't think they can.

I was worried. I was worried because I feel like, and this is something that people talk about a lot, but everything that fails on behalf of a startup is almost a personal failure. It's almost like you'd failed a test or something. If there's a conversation with this guy and I sent a bunch of emails and this guy didn't reply, I felt like I failed at something. I felt like there's something that I'm not good at and it's a reflection of me. It's like an indictment of my character almost. I think that was the motivator behind a lot of the things that I've done, which put me in a place where I was catching my breath. I would have anxiety and panic attacks. I think that was the driving force behind all of it. It was this inability to separate myself away from the startup and having a consumer life in that fashion. I would say ... I don't know how you can do that.

Probably what I found useful for me is meditation and forcefully pulling myself away from work multiple times during the day. I would reply to a bunch of emails, but just before my head started spinning, I would just go take a shower, or take a walk. I'll try to getting a bit of physical exercise, sweat time every day. Those things they would help ground you back into reality and it helps you to see your day is going well irrespective of whatever you need to deal with on the business side. I would first of all say that. Second, I think it's really important that you have a bunch of friends who you're able to chat to or to talk about ... That could be your parents if you're lucky. Having that support network where you had a terrible week, and then you can go to someone's house, crash, eat some food, chill out, come back and take on another week. That's very useful. I didn't have that back in second year.

I actually did the reverse. Because of the startup, I'd walk myself off from all of my friends because I thought, whenever I meet them they'll be asking you how is the startup going. And I don't want to answer that question. I don't even want to meet them. I would think I just got to hustle more and so I was very isolated. I think when you're isolated, you become a lot more fragile and brittle. If something shakes your foundation, you're just broken. I think it's important to have a few of those friends at the very least, preferably founders who's able to support you through that process. That's very important. I think third, I was way too caught up in executing things. If I need to get something done, I'd just get it done without thinking about why. What I could have done is learning a lot more. I could have watched a lot of YC videos a lot earlier, got to know what growth actually is. I could have gotten around to no-code platforms.

But I never really had the time to learn things because I felt this urgency to just get things done. If I need to send out 10 emails tomorrow, I'm like, "Okay. I need to wake up at 8:00. I've got to budget at this time." I wasn't even thinking about what's the best way to mass send emails. Maybe there's a tool that helps me do that. I think founders sometimes get caught up in this really terrible execution loop where they're always optimizing time to get things done. It's like ... My second co-founder actually taught me a lot about that. She would be like, "Why are we doing this?" It's only when we have a compelling reason, then we can be like, "Okay, let's figure out how we can get this done as soon as we can." But otherwise, you don't have to do a lot of stuff that you do. I think when startups are working really well, and that's something that you typically found out later on with some of the most successful founders, they just do one or two things and that's it.

They don't concern themselves with getting everywhere. Marketing, no, no marketing. Everything is talking to customers. Before you even get to the product, you don't even have to build anything, you don't even have the code. Just talk to customers, spend your time on the phone, that's it. Once you hit product-market fit, it's like code and growth hack. Try to find channels in which you can have the sustainable engine of growth. It's dropping everything else. Don't talk to VCs. Don't do marketing. Don't worry about competition. Don't go out for founder catch ups. Let's just do that. I think once you get to that place where you're able to crystallize all of your things into one bucket, things become a lot easier and it gets rid of a lot of the mental baggage that founders typically have. That's what I think worked really well for me. When things are going well, I'm doing a much less, but I feel a lot happier and I felt like I was seeing the direction for it.


Jeremy Au: (01:11:10)

Yeah. Obviously you're talking a lot about the what of what you'd tell your 18 year old self. Like what to do, what to respond if I'm just kind of curious, how would you have talked to your younger self? What would have been the tone? I mean, you know yourself as a recipient, you know yourself now how you get feedback. Would you be more direct? Would you be more kind? Would you be more Socratic? Would you do it over some beer? Would you just bring some.


Brent Liang: (01:11:41)

I don't drink beer. I'll probably do it over some tea, I think.

Jeremy Au: (01:11:43)

Do it over some tea. How would you have delivered that feedback in a way you think would have been received well?


Brent Liang: (01:11:50)

I would be very gentle. I think that's the mistake people typically make with talking to some of the Gen Z folks. All of the Gen Z founders I've met are extremely amazing. They're fascinating, and I cannot wait until five, 10 years later, what kind of stuff they can actually build? What people tend to not realize is, for the current generation of Gen Z, they grew up with a lot of chips on their shoulders. Even with social media, if I'm a girl, I have to compete with someone like Charlie where I don't even know where she's from. But her pictures, her TikTok videos are constantly showing up on my screen. There's a lot of competition, there's a lot of fragility, that's built into the fabrics of our Gen Z society. Because of that, I think one of the actual result you can see mental health going up, problems going up a lot. The dynamics tend to be a big issue when it comes to for the family with a Gen Z kid.

When it comes to giving feedback, I think you got to take in too some of the stuff into account. The typical boomer way of saying, "Okay, this is just what it is. Take it or leave it." It's direct feedback and it's just how we do things around here and don't take it personal. That stuff doesn't work. It's good intention, but it's executed poorly. Direct feedback is still very important. I give direct feedback to every single person who's in a team. When things don't work out, I talk to them. But there has to be some art in how you're delivering that, especially with someone who's young, like 18 let's say right now. But what I would do, is I would frame it in a way where I would explain the motivations of where this is coming from. I would talk about how I felt. For example, let's say, if you're a designer on a team and you're 18, or if you're a founder where your company's is failing or whatever and I'm an investor.

I would say like, "When you did this, I noticed myself feeling this way." Instead of saying, "I'm this, because you've done that." I think being able to pull yourself away from those observations, just give a very clear description of what's happening to you through you. Telling that to someone who's young and literally giving them a ton of options to improve, to change, or even give them places to go to get help or whatever, all of that, I would ... If I'm having someone who's failing at a designer job, I'll be like, "I can refer you to go to OnDeck to take a designer fellowship. Let me know if you want to ... I can try to find you sponsors, whatever." That's something that would get those people hyped. They would want to grow because that's the first thing that got them in to startups and whatever in the first place. I think it's, remove yourself away from the equation, communicating stuff in a much more gentle way, and also just relentlessly outline personal growth, next steps.

Whatever you can do to help that person succeed, that I think reciprocates when it comes across in a very authentic way when you communicate to a Gen Z audience.


Jeremy Au: (01:14:48)

Wow. That's amazing and, wow, I never thought about it that way. I think you're right, social media it makes everyone fragile because there's so much competition. Then plus you're 18. I think that's something I do have to reflect on as well. Yeah.


Brent Liang: (01:15:03)

That's actually one of the common criticisms about Gen Z people, Gen Z folks, is they're very easy to be triggered. I mean, I wouldn't want to say it's kind of true, but they are easily triggered. But you have to understand why. Why are we so fragile? Maybe for me, I'm easy to be triggered as well. Why is that the case? Because we've been consuming ... It's information overload from day one. We grew up with cell phones and we're constantly competing with people. I got my LinkedIn set up when I was 14 and I've been keep updating that ever since. Imagine being able to compete on likes and whatever you need to get on those kinds of platforms as you are 14? That's just a lot of pressure that build for you.

I used to have anxiety issues as well and I think I can relate to a lot of the things that's people are currently processing through. Tough feedback given in that really top-down fashion, expecting someone to not take it personal, it's just not the way to go forward with this Gen Z audience, 100%.


Jeremy Au: (01:16:03)

That was really helpful. Well, I think that's pretty much on time. I just want to say for those who want to carry on the conversation, you can go to There's a club to discuss this episode. But I want to recap, I think to me, I think the three most important parts I think from this conversation. I think for me, that really resonated for me number one was not about the failures or the success even, but I think it was your rate of personal learning. What you took away from each time and being very intentional about it, was really what stood out for me. That's one. The second thing that stood out for me was you doing moonshots and meeting demigods. I think it's a fun story, but it's also a nice way to think about it. Because I think at best people are trying to get an A or improve 5% every week.

I think I like what you said about moonshots as a very different approach. I think the third thing I like what you said was, I think you often talk not just what you do, but also how you would do it. Not about fixing problems, but your approach as a plumber and of course my contention, as well as explorer and editor. But you talked about your feedback about how you would help yourself as a first time founder, as a young one, versus how you'd approach it. I think that's something that so many people think about is, they're not thinking about how they give feedback, they're thinking about what feedback to give. But how is way more important than the what. I always tell people, it's like, "No one cares what words came out of your mouth during the feedback. It's either positive or negative. But how you deliver it is 99% of what they're going to remember." Awesome. Well, thank you so much. It was a pleasure to have you here.


Brent Liang: (01:17:48)

I appreciate it, Jeremy. I really appreciate it.