Han Yuan 0:00

So, Hitesh... I approached you some months ago about doing a podcast. Why did you say yes?

Hitesh Chudasama 0:29

You know what? For me, I've always been curious in regards to how people have gone through their journeys. And all the time when I look at LinkedIn, it's really polished. And I actually wanted to understand, what are some of the battles

Why are we doing this?

Hitesh Chudasama 0:43

people have gone through within their journeys? And when you approached me with the idea of doing a podcast with some of the leading executives, I was excited. I'm like, you know what? This would be fun to go ahead and do and be able to go ahead and learn but also the biggest thing is to be able to help others who are going through that journey at this time

Han Yuan 1:00

how do you know like when you think about like whether or not we're doing a good job like how are we going to figure that out

Hitesh Chudasama 1:06

I think it's going to be all based on feedback once we go through and talk with different people it'll be good to be able to get feedback from our audience to

What defines success?

Hitesh Chudasama 1:15

be able to see are we going down the right direction are we uncovering you know the right questions are we asking the right questions and is this something that's going to be helpful because I think for me, it's about trying to go ahead and make an attempt to be able to understand people's journey and see how we could go ahead and dissect it so others could learn from that as well.

Han Yuan 1:34

Yeah.

Why blazing your own career path is hard

Han Yuan 1:35

I mean, just thinking back to my own time, I kind of feel like a lot of times I went through some tough experiences and I just didn't know how to blaze that path. And I'm curious if you kind of felt the same way.

Hitesh Chudasama 1:47

Yeah. I mean, there's been many times where not just from a technology point of view, but also people process point of view where it was not a straight cut out solution and trying to go ahead and create your own path it's daunting and then not knowing you know it's still unknown so you're not sure what's going to be what's going to happen as you go through and make these decisions so but yeah I think I've gone through it but I think it's been a learning process along the way and not everything has been 100% so I think as I've gone through the different journeys it's gotten easier but still at a certain point I still find myself where there are unknown and I have to go ahead and figure out and make the best choice possible.

Han Yuan 2:28

I think that's totally legit because there are so many things that I think you just don't know what you don't know.

Hitesh Chudasama 2:34

Yeah,

Han Yuan 2:34

that's part of the problem. Like if I knew what I knew or if I knew what I don't know, then I could go learn it. Right. But sometimes you don't know what you don't know and you don't know if this has been seen before. And so I'm definitely thinking like if we can pull some of that information out from folks, that'll be amazing. So we've talked about this before. Like who what kind of people are we going to bring on this show?

Hitesh Chudasama 2:55

So for me, I wanted to go ahead and see if there are folks who are in the different levels of their journey from an executive perspective, not just in within engineering and product, but also in different domains. Because I think it's not just the fact that there's a lot of good habits that executives have done over the years across different domains. And we could learn from that, and the audience will learn from that

What types of guests can you expect to meet?

Hitesh Chudasama 3:19

as well. And I think for me, having somebody who has gone through the battlefield from a startup point of view, zero to one growth, as well as executives that have been part of large organization and building and scaling, I think these are some of the challenges that that our future leaders will be going through and they could learn from that as well.

Han Yuan 3:39

Yeah, I'm definitely hoping we also get some mid-level operators. So like folks that are managers, senior manager, director, or back when they were in those roles, because I would argue that if you look at the people who actually drive the big initiatives. It's not the person on the podium giving the fancy speech. It's these mid-level operators that are actually like shipping things at scale, solving real problems. And I think getting that like on the ground information is going to be clutch. Yeah,

Hitesh Chudasama 4:09

frontline managers will be great as well because they actually are going through the thick of things where they have to not only just execute, but also making sure of bringing everybody along, especially with their team and collaboration across different peers as well. So

Han Yuan 4:22

we're going to be doing our own individual episode, so we'll not spoil that. But maybe you could talk a little bit about like who you are and I'll take over the mic from there and we'll leave it at that for this.

Hitesh Chudasama 4:34

Yeah, of course. Yeah. I mean, like for me, I've been in the tech world for the past

Introduction to Hitesh

Hitesh Chudasama 4:38

over 20 years. I've gone from being part of a defense company when I initially started and then going to a startup world, totally different, where in the tech industry or at least in the defense industry, it would take at least three or four months to go ahead and start on the execution, while within startup at that point, going through the whole iterative process, where you're trying to go ahead and trial and error all the different experimentation and learning from it on an ongoing basis. So that was a great

Han Yuan 5:05

journey. I had no idea you were in the defense industry.

Hitesh Chudasama 5:08

While I was still in college, I was there. And the language I was working with was Ada. So working on embedded software, creating the software, going within actual Bradley tanks and installing it and being able to go ahead and verify your work. So totally different than going to, you know, full startup e-commerce kind of company where you're able to see your work right away. Yeah. So after that, I mean, I worked across different startups and then also I was part of the EDA company, which is the electronic design automation and then consulting for a wireless company within Santa Cruz. And then I joined eBay. This was in 2003. I was at eBay for quite some time and this is where I met you. Before meeting you within mobile, I was part of the eBay search team. And this is when eBay was going through a huge migration and then expanding on their search initiative. So I worked across all of that. We worked on major initiatives like eBay Express, and there was also eBay Wanted Now. Some of these products have been there, they came and gone. But it was a great journey. And then eBay Mobile, especially with you and some of the folks that we worked with on launching eBay Mobile. And expanding that across different countries.

Han Yuan 6:24

Yeah, those are good times for sure.

Hitesh Chudasama 6:25

Yeah. And then, yeah, from eBay, you know, joining you once again within Upwork. And I think the expansion, especially going through the whole IPO process. And I think for me, it was even though I was part of multiple different startups, this is the first time going through a full IPO process. So there was a lot of learning, but it was great. I mean, definitely very busy and challenging, but it was a great journey.

Han Yuan 6:47

Dude, you were on the money project. That domestic marketplace was in the S1 when we filed. When we started it, it started growing 1% week on week and the company went public 18 months later. So it's definitely something that you should be super proud of.

Hitesh Chudasama 7:01

Yeah, no, it was fun. I think a lot of great folks, you know, worked on this and then we were able to go ahead and learn through our customers and be able to expand that marketplace.

Han Yuan 7:11

Yeah.

Hitesh Chudasama 7:12

Yeah, so I think after Upwork, I joined another startup and then also Marpe Health. So changing up into health tech work, but then still focusing on marketplaces.

Han Yuan 7:22

Yeah, you've had a long career, lots of stuff. You've got the healthcare angle now, you've got the marketplace angle, and apparently you have defense.

Hitesh Chudasama 7:32

Yeah, back in the days. So I think that's something, things have evolved quite a bit, but I think it was great to get that experience.

Han Yuan 7:40

Yeah, and I think that's a lot of what we're going after, that when you build your portfolio of companies as you progress through your career, you're going to learn different things along the way.

Hitesh Chudasama 7:49

Yeah, even now, like playing a fractional CTO kind of role, working with different startups at different stages, I think I've been able to go ahead and learn from my background and being able to contribute. And each company has their own, even though you could classify it in a common kind of bucket, but then each company based on the different people and processes, you have to create some form of custom solution. You could start off with some base solution, but then you do need to customize it for each one of the companies. And that's one of the things that I've been finding is the fact that processes and technology. I mean, even though there's a lot of, you know, like awareness and education around it, but implementing it and getting the buy-ins and getting, being able to go ahead and leverage that and being successful at it, it does take time and getting people on board.

Han Yuan 8:36

That's right. A hundred percent. You know, as for me, I'm pushing 30 years of experience. I would describe my career as a bit of a trilogy.

Introduction to Han

Han Yuan 8:46

The first third, I was in enterprise software at tech and at Saba Software. A little known company, but it was featured or mentioned very briefly in the Benioff book. One of the characters was Bobby Izzani, and Bobby was the founder of Saba Software. Today, they are part of Cornerstone On Demand. I was also part of a company called Movaris, which was acquired by Trintec. We built Sarbanes-Oxley software. Along the way, I started a social network. We ended up selling it. for like you know 250k which frankly was a lot of money at the time for me and frankly still is now but it the the social network was awesome because it really inspired me to um get into more direct-to-consumer software. I had friends who joined that social network and then eventually marrying somebody that they met on that social network. So I was very inspired to start my own company. And in 08, that was a very bad time to start a company. And so that's, you know, sometime later, almost nearly being penniless, I ended up getting a life raft. And that's when I joined eBay with Mr. Yankovic, which you also know. And then that's how you and I met during the eBay mobile run. And I think in between my two stints at eBay, I also had the privilege of working with a pretty killer and frankly legendary team over at Netflix, many of whom are still there. And in the back half of my career, I was the head of engineering at Upwork. And then in more recent years, I've joined various smaller companies that have product market fit, pushing $100 million in revenue and looking to scale. So I consider myself a startup scaling expert. I'm not so much of a big company guy. I obviously did not spend that much time in big companies. I like to get stuff done. I like to ship things. And as you know, I tend to have a no BS way about me. So I'm looking forward to how you and I can bring these different perspectives and try to get some good stuff out of our...

Hitesh Chudasama 10:57

No, I'm looking forward to it as well. I actually did not know you had a social network startup. That's really cool. I'm kind of like, you know,

Han Yuan 11:07

in the play Hamlet, there are these two guys that are in every scene, Rosencrantz and Guildenstern. I'm like Rosencrantz and Guildenstern. I can tell you that... I have met Mark Zuckerberg. I have met Jack Dorsey. I've met Vinod Khosla. And always in some kind of random way, I was actually interviewed by all three of them for various roles. And of course, I'm still here.

Hitesh Chudasama 11:29

You're a badass, Han. I've seen you in action. So, I mean, the thing is, you don't give yourself that much credit, but I mean, I could tell you firsthand I've seen you in regards to both at eBay, especially within mobile, where there's There's a lot of pressure. And I mean, the way that you were able to go ahead and navigate through that and working with the different executives and making sure the fact that mobile gets the right attention. I think you did an excellent job. And especially also at Upwork. Upwork, I mean, even though it was a startup combination of two companies coming together, you had to do a lot, not just from a technology innovation point of view, but reconsolidation from a process people point of view, making sure the fact that we're able to go ahead and focus on the right things. So, yeah, I mean, it's a It's been awesome working with you and the journey that you have, it's been really diverse. And I know our listeners will be learning through all the different kinds of experiences you had as well.

Han Yuan 12:20

That means a lot to me, man. I heard this term recently about the importance of having a cold mind and a hot heart. And I've always put

Conclusion

Han Yuan 12:30

some value in that. That's something that I've always aspired to. And I think Thanks for having me. It shouldn't be this way. And I think getting some folks to join us as a guest and talk about the past, it might inspire people to do things differently.

Hitesh Chudasama 12:55

Yeah, totally agree. Yeah, I think there's a lot of experiences people have had across the years, across different industries as well. But how to go ahead and lead people, and especially through changes and transformation, I think there's going to be a lot of good nuggets that our listeners will benefit from.

Han Yuan 13:10

I'm looking forward to figuring this out with you, man. We're going to have a good time. It's going to be awesome. Looking

Hitesh Chudasama 13:16

forward, man.