We’re back with another episode in partnership with Insignia Ventures Academy (IVA), Asia’s first experiential VC accelerator! We went on call with Andy Hwang, former Google and Facebook go-to-market leader, now angel investor and startup advisor in Southeast Asia. He’s also an alumnus of IVA, and more recently has been a mentor for the second cohort of the program. We talk not just about the program with him in this episode, but also learn more about his career transition into becoming a full-time angel investor after many years in various big tech companies, and also get his thoughts on some of these emerging technologies from working with founders. Join him and other seasoned investors and operators in Insignia Ventures Academy’s growing community by applying for Cohort 3 coming this Feb 2022!

We’re also happy to share with our listeners in this episode a promo package from Aspire, the all-in-one finance operating system built for fast-growing startups. They’re offering the Insignia community an exclusive welcome offer for a limited period of 31st December, 2021. Startups will get a $250 cash reward when they open a new business account and make their first card purchase with qualifying merchants with the Aspire card, minimum of $5. Redeem the offer here.

Timestamps and Highlights

1. 00:51 Paulo introduces Andy Hwang;
2. 01:45 What wakes Andy up in the morning; “As I think and look through my career, I’ve always just had just a penchant for wanting to learn, and even now in my career, to optimize for learning.”
3. 02:45 How growing up in the Valley’s tech optimism drew Andy to Southeast Asia; “One of the reasons why I came to Asia and why I’ve stayed here in Singapore the last 10 years is because it reminds me a lot of growing up in the Valley in terms of the excitement, the founders, the ideas, and the capital all coming together.”
4. 05:03 Going international at Google then Facebook; “The thing is when you’re learning really quickly and the business is growing, it also means that you’re making a lot of mistakes. So you tend to get better at both making the mistakes as well as pattern recognition.”
5. 06:29 Learning the art of making mistakes at Facebook; “As I look at the journey of 10 years at Facebook and what I’m doing now, it’s about just compounding the little learnings over time. And with the business that we’re in now — early stage investing — you can still be wrong the majority of the time and do okay.”
6. 11:05 Deciding to be an angel investor and spending a year at Stripe; “I realized I ultimately want to spend the majority of my time with founders and to get back to that, I probably had to start my own business or do something in the investment community.”
7. 13:58 Positioning oneself as an angel investor in Southeast Asia; “And so [the] benefit for me right now, being independent, especially to start with, is that I’m able to move with maximum speed as well as flexibility.”
8. 15:34 Day in the life of Andy Hwang the angel investor; “…as an early-stage investor, oftentimes we’re not going to know whether we did a good or a bad job for quite a number of months, potentially even a few years. So it is really important every couple of weeks, just to reflect on how things are going…”
9. 16:54 Finding product-market fit as an angel investor; “In the same way that we talk a lot with founders about product-market fit, the last 10 years for me being here in Asia has been finding my own product-market fit, if you will.”
10. 19:32 Common pitfalls of early-stage startups; “…if you’ve got the right market, but a founder or a team that’s not great, they can grow into a good or a great team. That team can still win, versus, I rarely see cases of good teams in bad markets that win.”
11. 22:15 Developing investment rigor and discipline at Insignia Ventures Academy; “The majority of my experiences really were around working with founders to scale up and where I really wanted to build was around just the investing side.”
12. 26:58 Rapid Fire Round;

About our guest

Andy Hwang is a full-time angel investor and startup advisor, but prior to that, he spent a decade in Facebook, doing a lot of go-to-market in APAC, leading Facebook’s entry and into east Asia, especially, and then prior to that, he was at Google doing a lot of, marketing work there as well in some of these emerging markets like Latin America. He took his MBA at Wharton and was a graduate of UC Berkeley. 

Transcript

Paulo: On that note, Andy, what’s exciting you these days about — your day-to-day about your work and what wakes you up in the morning and what keeps you energized?

Andy: First of all, the actual thing that wakes me up every morning is probably around 6: 45 [am]. My kids are jumping on [me], asking me what’s for breakfast, but seriously, I do like to spend my morning having breakfast with my kids, taking them to school. 

And then from there the day really is about meeting with founders and partnering with them to build amazing companies. I have the privilege of doing that with a number of companies. And one of the best parts of my day is I never know what’s going to happen, how it’s going to end up. But I know that I’m going to learn. And as I think and look through my career, I’ve always just had just a penchant for wanting to learn, and even now in my career, to optimize for learning.

“As I think and look through my career, I’ve always just had just a penchant for wanting to learn, and even now in my career, to optimize for learning.”

Following Tech Optimism from Cupertino to Singapore

Paulo: I just want to dial back, given what you’re doing now and what you’re really excited about now, apart from your kids waking you up, [to] the fact that you’re working with founders 24/7. Was that something that you saw yourself doing, especially way back, even as you were growing up? You mentioned in the session that you did with [Insignia Ventures] Academy that you grew up in the Cupertino area in the Valley. Did you see yourself working with these like tech entrepreneurs in the future?

Andy: I don’t think I could have ever imagined back then what I would be doing now, but what I can say is that growing up in the Valley, I knew it would be something around tech. And so my parents bought me a share of Apple stock when I was five years old. And from that moment every morning, I would rush to get the morning newspaper and start to flip through [the newspaper] and then pick out the business section and look up the Apple stock and figure out why it had gone up or down.

I never would have guessed that that would have led me to Asia and to now working with founders. But what I did know is that technology was blossoming back then. And it’s one of the reasons why I think of myself as an optimist. It’s hard to grow up in the Valley and not be an optimist because I was seeing every day the promise of technology and what it could do for people, companies like HP and Apple. 

And I’ve tried to bring some of that optimism. Of course, it has to be grounded in reality. One of the reasons why I came to Asia and why I’ve stayed here in Singapore for the last 10 years is because it reminds me a lot of growing up in the Valley in terms of the excitement, the founders, the ideas, and the capital all coming together.

Paulo: We’re actually seeing the same kind of very infectious optimism happening here in Southeast Asia as well, which I guess is the reason why you were drawn towards the region and spending a lot more time here.

Andy: Absolutely. And nowadays I think about the reason why I came initially, which was to help set up the Facebook headquarters in the region with the landing team. But the reason why I’ve stayed is because of all of the trends from conversational commerce to really now the birth of Southeast Asia and the fact that now people can honestly say innovation comes from all over the world. Certainly not just from Silicon Valley. All the reasons why I initially wanted to come out to Asia are also the reasons why I’ve stayed and I’ve made my home here.

“One of the reasons why I came to Asia and why I’ve stayed here in Singapore the last 10 years is because it reminds me a lot of growing up in the Valley in terms of the excitement, the founders, the ideas, and the capital all coming together.”

Paulo: As the quote goes, the world is flat, or getting flatter at least. Speaking of launching Facebook here in APAC, how did you decide to [do it]? What was it your decision? I mean, coming up from Google and then joining Facebook, was it something that you really wanted to do, to explore Asia? Or was it something that you just sort of serendipitously landed with In terms of an assignment?

Andy: When I look back at my career Paulo, I think it is marked by an openness to trying new things. And when I joined Facebook back in 2010 at headquarters, [I] made it really clear from the beginning that if there was an international assignment that came up, it’s something that I wanted to be a part of. 

At Google, prior to Facebook, I was fortunate enough to be part of the team that worked on the Latin American business for search advertising and with a little bit of taste of the international markets, from my perspective, it’s something that I wanted to continue because I saw that there would just be a lot of opportunity, and of course more risk [as well], of building and going out to smaller markets.

And so when the opportunity came for Facebook, I said, “Wow, I’ve got to take this.” I just never could have imagined that that would have led to 10 years and literally hundreds of mistakes later, but a lot of learning. The thing is when you’re learning really quickly and the business is growing, it also means that you’re making a lot of mistakes. So you tend to get better at both making the mistakes as well as pattern recognition. And I try to carry some of those experiences now when I work with founders.

“The thing is when you’re learning really quickly and the business is growing, it also means that you’re making a lot of mistakes. So you tend to get better at both making the mistakes as well as pattern recognition.”

Paulo: Speaking of learnings, and as you phrase it, “making those mistakes,” what are the most significant mistakes that you learned from your efforts to launch Facebook the region here?

Andy: Gosh, there [were] quite a number of mistakes. So one of the classic ones that I made early on was to hire a leader for Japan because I was impressed with just the level of English. And it’s a classic mistake that new folks to a market make. And the reason why it’s often a mistake is the better somebody’s English is oftentimes it means they’ve spent more time out of their home country, versus in many ways you want to be hiring them because of that expertise in that home market. 

That was an early mistake, [made] many more with Taiwan, but I think the learning from those types of experiences is you make the mistake and then you learn and you move on and you don’t make the same one. And as I look at the journey of 10 years at Facebook and what I’m doing now, it’s about just compounding the little learnings over time. And with the business that we’re in now — early-stage investing — you can still be wrong the majority of the time and do okay. 

And so one of my favorite statistics often is from baseball, one of the classic American sports, where if you’re able to get on base just 30% of the time, basically if you fail 70% of the time, you’re still going to be one of the all-time best that’s ever played the game. And when I think about early-stage investing, it’s very similar.

We’re making [bets] on companies and founders. We don’t know which one will work out and we may be wrong the majority of the time, but it’s just about being clear and making good decisions so that a few of the bets end up paying [off]. 

“As I look at the journey of 10 years at Facebook and what I’m doing now, it’s about just compounding the little learnings over time. And with the business that we’re in now — early stage investing — you can still be wrong the majority of the time and do okay.”

Paulo: We always talk about 90% of startups failing and that’s pretty much almost become gospel in the startup world. But at the same time, along with that reality, as you mentioned, is also the reality that because startups fail that often, there’s also always that opportunity to make some changes or pivot or do something new, and work with the founders towards that. 

Speaking of your experience launching GTM strategies for APAC, and now as an angel investor, what do you tell founders from that experience that is really valuable to them, at an early stage?

Andy: Yeah, there’s a number of different lessons. Especially when I look at the time with Facebook, when I first came into the region, there were a number of markets such as Australia that already had traction. And then there were other markets such as China, where we didn’t have any business at all, just because we have no users in China.

And the team there did an awesome job of just building an export business from scratch into one of the largest businesses for Facebook in the region. So the lessons for the founders really are about oftentimes, first of all, having a vision or a hypothesis about a problem that you want to solve and the sides of the market from there, just trying a lot of different things, especially in the early [stages], and then in some way, executing your way into strategy. 

I think that the days of getting into a room with the whiteboard and saying, this is exactly how it’s going to work out, I don’t know that it’s ever played out as cleanly as that in the US and it certainly doesn’t play out that smoothly here in Asia. So it is about just making sure that the market is large enough, getting the right team, and then iterating yourself to success.

Paulo: I think the large part of that is, again, getting the right people, because that’s sort of the way that you figure out what works and what doesn’t, especially if you don’t have that experience in that market. So what do you tell founders in terms of hiring those right people to help launch in a secondary or third market, for example, or even work on commercialization or distribution? 

Andy: I think even before founders start their first company just being clear on what is the problem that they want to work with and who they have worked with in the past, or who is in their network, [with whom] they want to solve particular problems with, I think it starts from there.

And the reason why that matters is oftentimes the way that we draw it out in a deck for fundraising or a business plan is so different from how the business ends up. So it really is about how do you build a team that you ultimately want to work with? And then in particular, for some of the work that I do with founders, how do you become the type of founder and leader that other people want to follow?

When I think about leadership, it’s not at all about a title, but literally, as you move forward and you turn around, are other people following you not because they have to, but because they’re excited about where you’re taking them? 

“…just being clear on what is the problem that they want to work with and who they have worked with in the past, or who is in their network, [with whom] they want to solve particular problems with, I think it starts from there.”

Paulo: So changing gears a little bit, [and] going from Facebook and then now going into angel investing, and then, of course, spending a year in Stripe, what was that transition like for you? And how did you make that decision to eventually work with startups full-time as an advisor and investor? 

Andy: I do this exercise at the end of every year, [and] I probably have done this for the last 10 years where I asked myself, am I still enjoying what I’m doing? Am I still learning? If the answer is yes, great, let’s go on for another year. And near the end of my time at Facebook, I was still really enjoying what I was doing, but I was thinking back to what was the part of that journey that I enjoyed the most.

And for me, I came to the realization that it was the first year or two, building the APAC business in Singapore when the teams were small. And we were just building and making mistakes all day and near the end of my time there, it was much more about scaling and it also became a much more internal-facing role as well. So I asked myself, how do I get back to the place where I’m spending the majority of time with founders building their businesses? 

As companies grow the challenges change as well. And for me, I realized that I was much better suited to spending lots of time with those founders. And that’s really where I got excited. It was in the early days of working with them to scale their business, using Facebook and Instagram, and so at that moment, I realized I ultimately want to spend the majority of my time with founders and to get back to that, I probably had to start my own business or do something in the investment community.

And that’s what led me to leave and then start the business that I’m doing now, but in the spirit of optimizing for learning, as I was reconnecting with folks in the community and starting to meet with founders, the opportunity came up to build a risk team at Stripe. 

Although I had mentally prepared to start my own business, I took the Stripe opportunity because I said, I think I realized how important fintech already was and was quickly becoming in that I knew even a year or so at Stripe would give me the type of on the ground learning that would be so much more valuable than reading a lot of books or watching YouTube videos about. And so it was an awesome experience. I really appreciate what the team is building there. 

And then for me, I realized after a year there was still a lot more to learn. But I had what I needed to return and be a full-time investor. And nowadays, just the ability to focus on both B2B software-as-a-service companies as well as FinTech, some of that comes from the time that I spent at Stripe. 

“I realized I ultimately want to spend the majority of my time with founders and to get back to that, I probably had to start my own business or do something in the investment community.”

Finding Founder-Investor Fit as an Angel

Paulo: So in a way, Stripe was adding to your skillset and toolbox to be able to later on help founders across a variety of sectors. How did you position yourself, because obviously becoming an angel investor and startup advisor, you’re pretty much on your own and you have to work out everything, in the way that you engage with founders and try to get them to trust you and get your advice and all that stuff. So how did you position yourself coming into this kind of career trajectory?

Andy: I guess I was really fortunate in that regard, Paulo, because having been in Singapore and the Asian ecosystem the last 10 years, many of these founders and even engineers at big tech firms I had worked with or met with many of them. And so when I decided to go into full-time investing, it was more reconnecting with folks that I had worked with in the past. And nowadays, honestly, I don’t think as much about proving myself. Maybe that’s just me getting older; I worry a little bit less about that. 

And it’s more about how do I find the really interesting problems out there that people are solving? Either it’s a market space or it’s a particular country, and how do I just start working with them? Oftentimes it’s either through referrals or just through building relationships over multiple meetings. That’s really how I think about it. And so [the] benefit for me right now, being independent, especially to start with, is that I’m able to move with maximum speed as well as flexibility.

And so I don’t know if this is the right model over time. That’s where I’m going to just stay open, and just continue to optimize for learning. But I know, for what I’m trying to do now, which is to meet lots of founders and learn as much as I can, gosh, the past year has been fantastic in that regard.

“And so [the] benefit for me right now, being independent, especially to start with, is that I’m able to move with maximum speed as well as flexibility.”

Paulo: Maybe you can share with our audience what a day like in the life of Andy Hwang, the angel investor. 

Andy: I would say this on an average day, there are probably two to three founder meetings. Either I’m meeting them for the first time, or these are founders that I have already invested in their companies. And these are check-ins for those types of meetings. I’m trying to move them off of Zoom and just do more founder walks. I feel like when we get out there and we’re walking together, there’s a different type of energy. And so trying to do that more and more, that’s a typical day. 

The thing that I’ll say is, every couple of weeks I do try and take a day or [two], just with no meetings so that I can learn: learn about new spaces and just be intentional about how to spend my time, reflect on some of the decisions that I’ve made, some of the mistakes that I’ve made as well, and then also reconnect with some investors the community and plan for the next couple of weeks. 

So that’s part of the flexibility that I’m able to have now, because as an early-stage investor, oftentimes we’re not going to know whether we did a good or a bad job for quite a number of months, potentially even a few years. So it is really important every couple of weeks, just to reflect on how things are going and then to think about the good decisions and how to make more of them. [And for] some of the mistakes, really think about how do we learn from those as quickly as we can?

“…as an early-stage investor, oftentimes we’re not going to know whether we did a good or a bad job for quite a number of months, potentially even a few years. So it is really important every couple of weeks, just to reflect on how things are going…”

Paulo: How would you describe that add that you give startup founders and how do you balance that level of engagement or intervention across your portfolio of investments?

Andy: One of the good things about having worked in tech for a while is it’s become pretty clear to me all of the things that I’m just not good at. These are things that I either realize myself or people are constantly telling me like, “Andy, this is probably not where you should be spending your time.” And the flip side of that is I also get feedback on where I am adding value to founders directly from founders, after a session where we’ll talk about go-to-market, or about how to scale their team and org design. 

So in some ways, in the same way, that we talk a lot with founders about product-market fit, the last 10 years for me being here in Asia has been finding my own product-market fit, if you will. And the feedback that I get really is around go-to-market and people, culture growth, and org design. Those are the places where I’m able to work with founders and help them. 

“In the same way that we talk a lot with founders about product-market fit, the last 10 years for me being here in Asia has been finding my own product-market fit, if you will.”

Paulo: What has been your approach to that specific area of value add with org design, finding the right people, especially in early-stage companies and especially [with] leadership roles. Maybe you can share a story or a scenario that you’ve experienced.

Andy: Yeah, absolutely. So I work with a number of companies here in the region. One of the companies that I’m fortunate to work with is Novelship. So they are based in Singapore and they’re one of the largest online sneaker marketplaces, awesome founders with Richard and Chris. And so they have such a strong vision for what they want to see in the future and how I work with each company is a little bit different.

How I work with the two of them is oftentimes just sitting down and talking [about] some of the most pressing challenges that they’re facing? And they’ve got just an incredible background of being sneakerheads; where I try to round out some of their experience is how do we scale the team into additional countries? How do we help scale the company for additional fundraising? 

So it’s looking for complementary skill sets and that’s one of the things when I’m investing in a company or advising, just to look for founders that have complementary skill sets so that we know this is an area where we may be able to work together and I try and be upfront as much as possible, “These are the 10 areas where I’m probably not going to add a ton of value, but these are the one or two that think we might be able to work together on.” But at the end of the day, look, it’s not about the advisors or the investors. It really is about the founders, their companies, and their vision. 

“That’s one of the things when I’m investing in a company or advising, just to look for founders that have complementary skill sets so that we know, this is an area where we may be able to work together…”

Paulo: Given the many companies that you’ve already worked with, I mean, even in just the span of a year, what are the most common pitfalls that you’ve seen from your experience, investing in these early days of startups?

Andy: One of the most common ones is going to be around just the market. I really do subscribe to the theory that if you’ve got a great founder, but the market is not big enough or it’s not ready, the startup probably can grow to a certain size, but it’s not going to be able to scale to justify those venture backed returns. 

Even at the early stage, one of the mistakes that I’ve made is to think at times about the team and the founders before the market. But I really do think now it is about needing to find the [right] market because, if you’ve got the right market, but a founder or a team that’s not great, they can grow into a good or a great team. That team can still win, versus, I rarely see cases of good teams in bad markets that win. Ultimately what happens oftentimes is the team does okay. And then they might have a small exit or the company will fail, but then you’ll bet on that same team for the next idea or the third idea.

[That’s] probably the most common one that I see. And then the second one is about how do you choose your co-founders and then put your initial team together? I think one of the common mistakes I see is first-time founders don’t put enough time into vetting [how] their founders are thinking about their own skills and strengths, and how do they surround themselves with two or three other people that don’t look like them because as you’re building a company that diversity of opinion and approach is really, really important.

Paulo: Have you gone out as an angel investor to help find co-founders for these founders?

Andy: Oftentimes I do, [and] again, this is about founders and their companies. There recently was a case of a FinTech company and there was somebody that had a very strong background on the product engineering side. Another had a strong background, more from the finance and private equity side, but what they lacked was somebody that understood the risk and the regulatory space.

[For fintechs], these are one of the key areas. And so there was just a good conversation with the founders [about it and] I think we agreed that there was a need for that person. The conversation was about whether it made sense to hire this person as just an employee number two or three, or whether to make that person a co-founder and to have them vested in the beginning, with the rest of the co-founders. As you put this idea together, you attract additional employees and also bring in capital. My perspective was that a co-founding group needs to be really strong from a complementary perspective. 

“…if you’ve got the right market, but a founder or a team that’s not great, they can grow into a good or a great team. That team can still win, versus, I rarely see cases of good teams in bad markets that win.”

Learning by Doing at Insignia Ventures Academy

Paulo: So moving on from, talking about all these experiences that you’ve had working with startups, I’d like to also talk about your time in Insignia Ventures Academy, which was how we got to know each other and, so why did you decide to join IVA? 

Andy: It goes back to just wanting to learn. And about a year, or a year and a half ago, I realized as I wanted to do more working with founders, the majority of my experiences really were around working with founders to scale up and where I really wanted to build was around just the investing side.

So, I had an awesome experience through the academy meeting you and just some of my cohort mates as well, working with founders, but also being forced in the best possible way to pitch companies to the investment committee. Again, I’m a big believer that the best way to learn is by doing and not necessarily by reading or watching.

And so just having that pressure of pitching real startups was an awesome experience. And to this day, I still keep in touch with the folks that I’ve met through the program and some of the startups as well. 

Paulo: What was the highlight of your experience across the 12 weeks?

Andy: I think it was probably just meeting in my smaller group. So the way that the Academy works is we each get put into groups of four or five and just the preparation and getting to know each other, I did feel a little bit like a mini investment team and having the community of support and encouragement was really powerful for me. And even now I keep with the folks there, I think you had Mohammed on a couple of weeks ago.

Paulo: How has the program influenced you in that regard? Because you were already transitioning into becoming an angel investor prior to joining IVA I suppose…

Andy: Where IVA really helped me the most was just the discipline of not only meeting with founders, but also justifying, what was it about those companies, whether it’s from a product, team, [or] market perspective, writing down what some of the assumptions were almost as if we were working in a VC firm.

And the reason why that was useful is it’s allowed me to learn, but also now maintain that same level of discipline, now [that] I’m investing my own capital and I’m not presenting to an IC, just the act of being super disciplined, about how I think about investing. When I say no, why is that? And when I say yes to an investment decision, making sure that I do the appropriate due diligence. So I think it’s helped me introduce rigor to the investment process. And that was something that’s really helped me now, as I’m independent. 

“The majority of my experiences really were around working with founders to scale up and where I really wanted to build was around just the investing side…it’s allowed me to learn, but also now maintain that same level of discipline, now [that] I’m investing my own capital.” 

Paulo: Speaking of what you’ve learned from the program, do you have any advice for tech operators out there who are looking to angel invest, especially here in Southeast Asia?

Andy: One of the first pieces of advice, and I try not to give too much advice a lot of time [because] that may be wrong, and I know for each of us, we have a different path, but I really am a believer that the best way to learn oftentimes is through doing. And so the analogy I’ll give is this. 

For many of us, we went to school in university and when we paid our tuition to the university, we paid a certain amount of money [and] in exchange, we learned something. When we were done learning from the university, we would have never gone to the university and said, “Hey, I want some of my money back.” 

What the tuition was in exchange for learning, and that was, for the most part, theoretical learning, but with angel investing, I do think the best way to learn about this is not to just read about it, but it really is to invest in a couple of companies and then learn about the journey and the experiences, and then learn the mistakes, but in a real world setting and then adjust and iterate as you grow. 

It’s not necessarily about making 50 to 100 bets initially, but it is about making the first couple of choices because doing it in actual companies and trying to work with the founders is a lot more valuable than holding a virtual portfolio. 

“It’s not necessarily about making 50 to 100 bets initially, but it is about making the first couple of choices because doing it in actual companies and trying to work with the founders is a lot more valuable…”

Paulo: Yeah, thanks so much, Andy, for having this conversation with us and going on call with us. And now I’d like to move into our fire round and ask a couple of quick questions and you can give some short and sweet answers. but first a message from one of our portfolio companies.

Aspire is an all-in-one finance operating system built for fast-growing startups. It is an easy, fast and scalable finance stack with solutions that include company corporation, business accounts, corporate cards, FX, revenue management, and spend management. Everything you need to get your startup up and running and to scale globally, packed into one single account.

And now they’re offering the Insignia community an exclusive welcome offer for a limited period of the 31st December, 2021. Startups will get a $250 cash reward when they open a new business account and make their first card purchase with qualifying merchants with the Aspire card, minimum of $5. Redeem the offer here. 

Rapid Fire Round

Top 3 Skills of an angel investor?

Andy: Long time horizon. Two, have good instincts. And then also to be focused on the areas that you know.

Quick thoughts on the metaverse? 

Andy: I really look at the metaverse as being the new operating system. In the same way that people think about Android and iOS today, I think within a couple of years, that’s how people will be describing the metaphor. So it’s really a platform that the next generation of companies can be built on. 

Recommended book for founders and/or investors? 

Andy: I try to read as much as I can, frankly. I try to read across a lot of different areas, not just investing, but on philosophy. And for me, that’s just one of the ways that I get really energized is learning about what other people have done. 

Paulo: Are there any non-startup-related books you find very useful for you working in the startup ecosystem? 

Andy: One of the interesting ones I’ve read lately, it’s called “Bill and Dave”, it talks about the founding of Hewlett Packard. Growing up in the valley, Hewlett Packard was the Google and the Yahoo of the day. They were the ones innovating. The thing that many people who didn’t grow up in the Valley don’t know is that when we think about something that’s quintessential Silicon Valley now, from casual Fridays to profit sharing, to even sitting in cubicles versus offices, all of that came from Hewlett Packard.

And it was adopted later on by Yahoo, Google and other companies, even the buying of the land where you can hold annual retreats like that gets traced back to HP. And the reason why I enjoyed that book a lot lately, is number one, just to be reminded of what companies were innovative back in the day. But secondly, it’s also a warning sign as well that if companies don’t continue to be innovative, then they’re really going to lose their luster. And you look at what HP is today, it’s so different from what it was in the past. 

And one of the things I remember early on from my experience at Facebook, Facebook sign at headquarters in California on the other side of that sign is the old Sun Microsystems logo and something that the company specifically did in the early days when deciding [what] sign to use, other than the fact that the company didn’t have a lot of money, if they just turned that old, Sun Microsystems [sign] around and they made it into the Facebook sign as a reminder of what happens when companies stop innovating. And it just served as a warning signal for us, even as the company became more successful, we didn’t really focus as much on that and we focused much more on what is ahead that the company still wanted to accomplish rather than all of the successes from the past. 

Paulo: Do you think it’s inevitable in a way that these things happen eventually, like there’s always this turning of the page and, nothing really lasts forever in that sense, and it’s sort of nature that you do become complacent in that sense even from an organizational level?

Andy: For the most part, technology moves so quickly we don’t often see companies that are innovative and then they lose their window of influence. And then they enter a new age of being innovative. We almost never see that a couple exceptions number one would be IBM where they dominated the hardware space.

And then a lot of competitors came in, but then they reinvented themselves with IBM services. The other example would be Microsoft where they really dominated the operating system space, the productivity software, and then they lost their way. And then with Satya coming in the last few years, it seems like they’ve gotten that clear direction about moving to the cloud. But for the most part, we rarely see companies ever lose that window of influence and lose their innovation and then find it again.

Paulo: From the examples that you gave, like IBM Microsoft, it was always really about a change in leadership, bringing somebody who could bring in some new ideas or new approach to the company…

Andy: It’s somebody fresh, but they don’t have to be new to the company. It’s just somebody that realizes there’s a difference between the profits that the company makes today, but also a company can be both maximizing profits, but losing influence and innovation at the same time. So it’s just, having a leader that’s willing to make a bet on the future rather than continuing what’s going on now. 

Going back to the rapid-fire round, what do you do to de-stress?

Andy: Yeah, for me, it’s probably going to be going back to either reading or hanging out with the kids. So my kids are still on the younger side. They have so much energy. And the great thing about kids at this age is they really don’t care what I’ve been doing earlier in the day. They don’t care whether it’s been a good day or a bad day, but they just want to hang out. 

Paulo: And are you buying them any stock? As your parents bought you some Apple stock. 

Andy: I haven’t gotten the money stock yet, but I’ve been doing a monthly finance class with them. It’s never too early to teach your kids about compound interest. So I’m taking that to heart. 

Anything else you’d like to share with our audience?

Andy: In terms of just founders and fellow investors, the thing I would say is optimize for learning. Oftentimes, it’s so easy to get caught up and think about where the best short-term opportunity is, where I can raise the most capital, or here’s the space that I really should be starting a company in, because this is what’s getting all the funding, but try and just have a much longer perspective.

For each of us, what are the things that we enjoy doing? What are we good at doing? And how do we get to a place in our lives where we’re spending the majority of time doing that? Because if each of us is able to do that, we’re going to have some pretty incredible companies built here in the region and have some awesome investors that really do provide value in this ecosystem.