John-Simon Purcell on Startup Counterculture, Career Breaks & Standardizing Fundraising - E61

· Executive,Europe,VC and Angels,Podcast Episodes English



"Travel itself to me is this ultimate skill builder, because so much of our lives are spent again, communicating with other people and in different cultural contexts. And if you can master that way of communicating better and communicating with others, you're going to go farther in both your professional life and your personal life." - John-Simon Purcell


John-Simon Purcell (‘JSP’) is Senior Director, Product & Technical Strategy at Prosus Group/Naspers where he advises on new venture investments and provides operating guidance to Prosus’ worldwide portfolio in the areas of product, growth, and technology.

Prior to Prosus, JSP was Technical Director at Medialets, where he scaled systems to collect & analyze data for a product that was at one point on 85%+ of all iOS and Android devices. JSP had also guided Nokia’s Ovi Store, a B2C mobile experience with on-device and web based storefronts for billions of customers in every corner of the globe. He also held several technology leadership roles at MTV Networks and Sun Microsystems

JSP started his career at Cambridge, MA startup Vermeer Technologies which was acquired by the Microsoft Corporation. He holds a B.A. from Boston University and a M.S. from Columbia University, in Computer Science respectively.

Jeremy Au: [00:00:00] Welcome to Brave Dynamics. This is your host, Jeremy Au.  Leadership is harder than it looks. As a proven founder and Harvard MBA, I interview courageous entrepreneurs, executives and investors every week. I also share my frontline experiences, coaching insights and own professional development journey. If you're stepping up as a new leader, founding a startup, or venturing into the great unknown, this is the podcast for you. 

Hey JSP, really excited to have you on board the show. We've had a tremendous week over Clubhouse chatting about Southeast Asia and hearing your experience. And I'm excited to share your experience with the rest of the world.

John-Simon Purcell: [00:00:43] Thanks for having me, Jeremy, tonight. I'm really, really excited about this.

Jeremy Au: [00:00:47] Awesome. For those who don't know you yet, how would you describe your professional journey from university until today?

John-Simon Purcell: [00:00:55] Oh, a bit unusual. I'll give you a little bit of my background, some of which is actually not LinkedIn because I was fortunate enough to start my career at a Cambridge, Massachusetts startup called Vermeer Technologies that was acquired from Microsoft for about, I can't remember it was $133 million, $135 million, right before I graduated from university.

Now, $133 million might not sound like much now, but at the time it was like when Facebook bought Instagram for $1 billion, heads turned, mics dropped. From there, I made a leap from the empire to the rebel alliance landing at Sun Microsystems to work on the Java RMI or Remote Method Invocation project. Probably the longest lasting impact out of this was the adding of the Reflection APIs to the language without which there would have been no SpringSource or ATG, which is another company, a similar company that was sold to Oracle.

And this also forms the basis for almost all alternative languages on the JVM, so just Scala, Kotlin, JRuby, et cetera. So if you really want to get into a very long conversation with me, we could go into the intricacies of between Scala and let's say, Haskell at any time.

Sun was great, but it really didn't provide me with the consumer curiosity that I craved. And so after a couple of years, I joined Viacom, of all places, in New York City and stayed for a number of years, working on everything from physical and digital e-commerce for Nickelodeon and MTV, think toys, skateboards. I worked on the Zoom project to compete against the iPod for Microsoft, to real-time interactive television gaming until eventually running their platform engineering group on a global basis.

After about seven years or so, I think, the itch got hold of me and I needed to travel again. And I took a year off, wandering around the globe a bit and ended up at the Finish giant Nokia where I worked running their app store for their various drawer full of different mobile devices on S60, X40 range devices, you name it. But unfortunately, Nokia's internal politics at the time for me weren't so great. So it didn't take much for a friend to convince me to jump back onto the startup bandwagon.

And I eventually ended up at Medialets, which was at the time, one of the pioneers of mobile-rich media advertising and tracking. And the company eventually split into two. You have to love startup politics as well, with half of the company becoming Quattro Wireless, which was acquired by Apple and becoming iAD and the other half being acquired by WPP, which is the world's largest advertising firm.

The road beckoned again, and I spent a couple of years immersing myself in what I like to call startup centers around the globe, such as Berlin, Kiev, Bangkok, Mexico City, et cetera, getting deep into the various product and tech communities similar to what we're doing right now on Clubhouse. Back then, I worked mostly pro bono or for equity as American citizens and green card holders are, let's just say, under an interesting definition of freedom when it comes to assets and taxation outside the United States.

In late 2014 or so I think, it was probably around November, Naspers, who I really never heard of before out of South Africa came along and asked if I would like to do the same thing for them, but be based out of Amsterdam, I mean the Netherlands, because their portfolio span the globe. After digging a little bit deeper into their insane portfolio, I hopped on the opportunity and here we are.

And I guess just a last comment on this piece right now, for those of you listening in the audience and wonder how do you break into the VC industry or any industry really, that can be one way of doing it. Always having an attitude of, " I'm here to help for the startups themselves or for VCs," and really be willing to roll up your sleeves, get to know the players in your area, build a reputation. And they'll reach out to you if you do.

Jeremy Au: [00:05:10] Amazing, what a long experience and I think a ton of depth of an expertise in the startup world. Now, let's go all the way back to the beginning. So you were in college at Boston University, and then you took your first job at a tech company. What was that like? Was it like a no-brainer or was it something that you were like, "Oh, this is something strange"?

John-Simon Purcell: [00:05:31] It was kind of funny because when I first started my degree, I really wanted to be a history major, more than anything else. Really, that's my side passion in life is really a bit of culture and travel nut. And that changed around probably my sophomore year. And then I figured, "Oh, I'm really good at computers. I really love electrical engineering," because I'm the black sheep in the family. Almost everybody in my family is civil engineers.

And so I got into computer engineering, which is really about hardware and software. I think it was my senior thesis, which was, can you design a car braking system both with hardware and software that I realized that, "Oh, wait a minute. If I screw up something here, I'm potentially going to get somebody killed," like the braking system fails, they slam into a tree, and that's the end game.

And for me, I like to always think about the other person. And so that was a trade-off I wasn't willing to take. So I just stuck to the software side of things and somebody reached out and said, "Hey, we need someone to work on this, WYSIWYG HTML editor to bring the web to the masses. And I was like, "Oh, that's a great job." It's a part-time job. I can just go over the bridge to Cambridge, work at it. And then go to school at night.

And Microsoft came along, bought 25 of us and a Basset Hound. A day after I finished school, I hopped on my motorcycle and drove cross country to Seattle. And it went from there.

Jeremy Au: [00:07:07] What was it like to make that move, to pack things up and do that drive?

John-Simon Purcell: [00:07:12] The drive itself is amazing. The US is just a vast, expansive place and culturally so, so different in different parts of the country. I'm originally from New York City, which is really, really culturally diverse, especially with first-generation immigrants. We actually are the second, most linguistically diverse place on the planet earth after Papua New Guinea with 800 plus languages. And for those of you who are Indonesian in the audience, we actually found the last two native speakers of Indonesian language in Queens, New York, a couple of years ago.

Contrast that to vast parts of middle America, the Corn Belt, the Rust Belt, which is very, very different. And so it was a good learning experience for me to do that.

Jeremy Au: [00:07:59] And tell us more about your first day at the first company. What was it like walking in day one?

John-Simon Purcell: [00:08:06] I think, at least going to Microsoft was super, super different than compared to Vermeer itself. So the company that I was at is called Vermeer Technologies. It was named after the Dutch painter, Vermeer. There's a Dutch thread running through my life. And that really sort of gets into that really one of the hurdles to some extent that you can kind of overcome because when we got acquired by Microsoft, at the time, it was run by Bill Gates with Balmer waiting at the wings.

And needless to say it was a really toxic environment that valued the best idea IQ-wise more than anything else. And our experiences at Vermeer on being integrated into Microsoft team were so extraordinary in terms of counterculture, that they actually became the basis of a ten part Harvard business school case study. And as a young impressionable engineer, it took me a long time to distance or called deprogram myself from Microsoft's ideas at the time on how to compete in the software industry.

And it was really my start at MTV, which is a much more design-led company that really opened my eyes onto how culture can make or break a company. That said, I'm in total awe of how Satya has turned Microsoft around starting with the culture and made Microsoft great again, just a Herculean effort and hats off to him.

Jeremy Au: [00:09:30] Let's go into that. So you're starting to compare and contrast the cultures and at MTV, you started to learn a little bit more about what you felt was a great culture and a different take of it. What was that experience like personally? What were you learning personally in that new role?

John-Simon Purcell: [00:09:48] To be honest, I learned just how much of an idiot I was based on the programming that Microsoft had drilled into me because I wanted to advance at Microsoft. At the time, it was the greatest software company on the planet earth. Remember, this is like 1996, 1997-ish kind of thing. I'm in my late-40s now. And their impression of it was very much like dog eat dog. It was almost like a kill zone when ideas got thrown out and people would compete against each other to have their idea went out.

And you contrast that to MTV, which is much more chill and much more design-led and really about what the end customer wants more than anything else, I took a decent amount of time, I would say a couple months, and probably a couple of stern talkings from my manager to really realize that. I had to realize that my emotional intelligence wasn't as high as it should have been or was previously to my time at Microsoft and needed to be re-calibrated.

And needless to say, I always go deep now on how corporate culture is or is not a part of a company's onboarding process, both during our investment due diligence process or in potentially taking a job myself. My opinion is that startups need to really have a laser focus here as problems only get bigger and worse as the company grows. That also goes along with clear communication lines and methods as well.

And all that culture communication, all that stuff is tightly wound up with your onboarding experiences. And here in the Southeast Asia Tech Club, we're a super fortunate to have Jordana Valencia from Grab as a member, who is extremely articulate on this matter. And I encourage everyone here to follow her. We spoke on this at length a couple of days ago, and she just blew my mind away on it. Super, super impressive.

Jeremy Au: [00:11:55] Yeah. Well, she'd be coming on as a guest in a few months' time.

John-Simon Purcell: [00:11:58] I was going to suggest that, so good idea. Please people tune into that one and in all seriousness, she is fantastic.

Jeremy Au: [00:12:05] Yeah. Well, definitely, follow JSP and follow Jordana as well. A lot of people, obviously in the group, the crowd, the people, listeners, all of them go through feedback sessions. And I'm just kind of curious, obviously, I looked at you as a mild demigod. And so, walk us back to that.

John-Simon Purcell: [00:12:24] Completely, no.

Jeremy Au: [00:12:26] I know, but walk us back to your first set of feedback sessions, at MTV Networks. What was it like? Did your mentor or manager take you out to coffee? Was it like an impromptu feedback or was it like a whiteboard kind of room and they sat you down in a formal feedback session on that?

John-Simon Purcell: [00:12:44] Well, first and foremost, now I have a wife that I've been with for 20 years. And she can tell you how I am definitely not any kind of demigod and writes me off immediately. So that's first and foremost feedback that I get every day. And I think that's really where it comes into key place is to know who can give you real-time feedback all the time.

So it's like one of the markings of a really good supervisor is someone that will give you slight adjustments all the time. You're already riding the bike. You're starting to wobble a little bit here and there, and they're giving you little pushes and shoves just to make sure that you dump the bike and you're on the straight and narrow path. And then secondly, I think that you need is more of someone who can sit down with you and potentially talk about longer term and more aspirational goals.

I think a case in point really is more a lot of people struggle with work-life balance, which just affects all of us with those high performing careers. And I myself, I remember vividly, I think it was October 2018 on Thursday. I was in Easter Island in the South Pacific with all the Moai heads and those kinds of things, and was heading home to Amsterdam on which is at least a 27-hour journey via Santiago to Chile and Buenos Aires.

And when the KLM flight touched down in Amsterdam, I got a message to please book the next flight to Jakarta. And 12 hours later, I was on the 15-hour direct Garuda flight to Jakarta. So, think about this, within 48 hours, I traveled three quarters of the way around the globe. And now it's a Monday and I'm supposed to help out with a very large potential investment for the week.

Clearly, I needed to look at my work-life balance. Otherwise, it was a bit of like what the Japanese call karoshi or like death by overwork. And afterwards, I talked to my sister who is an educator and a single mom with two kids, and shout out here to all the moms, particularly the tiger moms in there as the ultimate authorities on that work-life balance. She reminded me that the only thing in life that we can control is ourselves and our own behavior.

And thinking in terms of emotional intelligence there, and self discovery helped me classify my behaviors into positive impact ones and negative impact ones. For instance now, I avoid all caffeine and alcohol on the road as I was using them to counteract what we call permalag or constant jet lag. And they were negatively affecting my behavior.

It's always going to be a work in progress, but the key thing is to really build your self-perception and your emotional intelligence. Journaling is a great way of getting started for this, for the why's as to what you're doing. And sometimes the quantified self-movement or trackers can add to this to really put in the how's as well into what you're doing and your behavior.   

Jeremy Au: [00:15:38] And so you received a lot of feedback while at MTV Networks. You spent seven years and a half there. What did you learn across the different stages? That's a long chunk of time, to spend in one company. We don't see that much nowadays. So would you say that you learn at different phases within those seven years?

John-Simon Purcell: [00:15:58] I'd say, yes. And I learned quite a bit in these larger chunks of times, but when I reflect on myself, like I've said before, in some ways I've had an unconventional career. I'd been at startups in mega nationals. I'd been a migrant worker in multiple countries. I've been a lifelong cultural travel nut having been to 52 countries.

And for me really, I'm a big proponent of career breaks or mini retirements in certain ways, if you can afford to do that. Really because it's these gaps between these big oceans of time that we spend at startups or corporate jobs that demand that often define us and provide us with new directions in life and to take advantage of them as you can. Because otherwise what happens if you spent seven years in your startup and it flamed out? Are you taking some time to sit back and reflect on what went wrong there, what could I do better, or what do I want next in life?

I think those are really the bigger moments and the less about the actual journeys when you're in a particular startup or a larger multinational or a corporation or something like that.

Jeremy Au: [00:17:09] So it's not just advice you're giving to people. You did it yourself, right? You traveled around a world for a year and three months. What was it like?

John-Simon Purcell: [00:17:16] I've done it actually multiple times in my life. So I think one of the core threads running through my life has actually been the exploration of other cultures. I think with my ... I can't remember, my first international trip was at age five, ironically enough, to the Kingdom of Saudi Arabia, which is not exactly on everybody's tourism bucket list these days; and Egypt, and this was, I think, the late '70s. 

It's that insatiable curiosity that leads to respect in others, which in turns makes me a keen observer of people. I'm the person at the party that can easily move through various different conversation groups and equally contributing to them all. My curiosity as well as my love for history gives me a wide breadth and depth of knowledge of many different subjects, be it product tech, finance, et cetera. And I think some of the greatest insights and experiences and opportunities often lay outside of the boundaries of our organization's comfort level.

For example, my first leadership experience with real consequences came when I was about 25 and visiting my then girlfriend, a PhD student biology in the gorge area that separates Ecuador and Colombia, which at the time was somewhat unstable with the FARC or a rebel military group against the Colombian government. Now, I'll spare you the whole story of trying to get her and her first year undergraduate students out of the country, which involves two erupting volcanoes, I think. It was Tungurahua and Pichincha.

A military coup d'état, lots of guns, bribery and a young student, who of course lost her passport just as we are about to step into immigration from the plane to Miami. But if you've seen the movie Proof of Life with Russell Crowe, it set in the same area, the world around the same time. And it kind of went a little bit like that except that I have pictures as my proof.

Travel itself to me is this ultimate skill builder, because so much of our lives are spent again, communicating with other people and in different cultural contexts. And if you can master that way of communicating better and communicating with others, you're going to go farther in both your professional life and your personal life.

Jeremy Au: [00:19:24] Wow. Thanks for sharing that. I'm just kind of curious out of all your travels around the world, what was your favorite country to visit and why?

John-Simon Purcell: [00:19:32] My saying is that there's no bad places to go, just bad timing. So I think 2012-ish or so, I took about three years off from my career if you don't count the time working with various startups at that time pro bono. And I just got lost in China and followed the Silk Road all the way through Central Asia, including Afghanistan and the Wakhan Corridor, which is breathtakingly beautiful. Up, down into Iran all the way up until eventually Istanbul.

And when you think about the old '70s, hippie trails and stuff like that, the timing for that was really great. And you could really meet some amazing people and cultures along the way. And now, certain parts of that may be unstable. Syria is a perfect example. If you went there in 2008, it was fantastic. If you went there in 2014 or so, not so much.

So I don't really have a favorite place per se. It's just about where your passion leads you and is the timing right for that? And if not, wait around and go when the timing is right. That being said, China, Southeast Asia and India in particular, you can go back again and again and again, because it would take lifetimes to explore any one of those three regions because they're so culturally diverse both in terms of the food, the people, the culture, those kinds of things.

Jeremy Au: [00:21:03] Wow, that's really interesting. You've had a lifelong interest in history and culture. On a similar note, are there any particular themes of history you're particularly interested in?

John-Simon Purcell: [00:21:13] It is cliche that history repeats itself, but in certain ways, it does. And that applies to our industry as well. I think this is what the third AI boom that I've experienced, followed by there's two winters. I mean, I have a master's degree in artificial intelligence and so I could speak kind of candidly of this one. Our technology basis is a bit cyclical because unfortunately, and I say this as the dinosaur in the room being in my late 40's, is that there's constantly new blood coming into the industry.

And especially in the Californian context, there tends to be a lot of ageism. And that pushes out unfortunately, older men like myself, but the real crime there is for minorities and women who, let's say, choose to have children or something like that, as if choosing to promulgate the human race is a bad thing.

And then they've gone in and come in into the old bucket again. If we look at Facebook, and all who get picked on Facebook, the average age there is 27. So if I joined Facebook, you have to hire a six-year-old or a seven-year-old to make that average again. In a lot of ways, as a result of that, there's a ton of new talent that comes in time and time again.

And sometimes there is genuine innovation, but sometimes it's just stuff that was invented before. We're under constraints and that's what all good engineering is. And it differentiates it from applied science is that engineers live with this thing called constraints. Gravity is a bitch. Without it, we could all go move at the speed of light. Where under those constraints at the time, we had the right ideas, but we couldn't make it physically go to the fruition to make it a reality.

Again, going back to this AI stuff, what's the biggest game changer? It's not necessarily the algorithms per se, but it's the fact that we have near unlimited storage and near unlimited compute power with our cloud infrastructure services, which is something we just didn't have before. If you look at the Go programming language, its signature feature is CSP. And that was created in 1977, '78, correct me if I'm wrong. But it was really a fresh concept when Go came out a number of years ago.

Jeremy Au: [00:23:32] What's it like to see the languages come back and resurface and be rediscovered? How do you feel about that?

John-Simon Purcell: [00:23:39] I think it's actually a fantastic. My only caveat on things is you don't want to get people who are like, and I see this in the old school Lisp community. Which is like, oh, Lisp is the ultimate and nothing can be done with Lisp and those kinds of things. And there are very large systems written in Lisp. The actual all-flight dispatching is done by a giant Lisp image.

That being said is that we don't want to get into that mindset of, " Oh, I fallen in love with my solution." We need to fall in love with the problem because the solution is going to get thrown away constantly as we learn more and more about the problem. So this applies to startups in their journey from, let's say, pre-seed all the way to IPO. When we look at companies or at least how I look at companies, I should say, nobody expects you to get everything right at the seed stage.

And so, we expect that you're going to throw out parts of your product, parts of your technology as you go through each round, because that's a sign that you're learning, you're gathering new knowledge about your problem space altogether. And so you think to yourself, "Oh, wow. The way I did the last time wasn't as efficient. Let me do it again. And I'll get to a better take on it at this point."

I don't know how many of you guys know, Ajey Gore, who used to be the group CTO over at Gojek. He has actually fantastic talk about this, about like ... I think this was at Singapore's GopherCon 2018, where he gave a talk on 11 lessons for building an engineering org at scale, especially in hyper-growth mode. That's fantastic.

And then there's also two articles. One is how Gojek manages a million drivers with 12 engineers from about the same time, that was a blog post. And there was also the CMO actually gave a talk on what rewrites look at Gojek. And again, just to be public here, Prosus is not invested in Gojek. But I thought that those were really, really great examples of teams that have fallen in love with the problem and not falling in love with their solution. And so they were open to always re-optimize things and scale the org and scale the business. And you can see the result right now.

Jeremy Au: [00:26:03] So how do you keep on top of all of it. I mean, you're obviously running off the things you've learned in university. You've done it yourself, as a programmer, as a technical leader and manager, as a VP. There's so many languages coming out, so much innovation is happening all the time. How do you stay on top of it?.

John-Simon Purcell: [00:26:24] For me, it's just insane curiosity. And like I said before, I can sit down in a room of lawyers and we can go through the specifics of legal contracts for how to renegotiate cloud services. What are the gotchas that you need to look for in the contract itself? What are some of the issues that are there? And that's me educating the lawyers who really don't have a product or a tech background about some of the issues that may come up.

And this is key both if you are a startup and you want to take advantage of some of the discounts at a cloud service providers, but then also if you are either trying to combine companies or trying to disassemble them and sell parts of them off. My interests are just all over the place and that's a good thing or a bad thing.

The good thing is I'm highly effective at what I do and for helping people. And that's one of my general passions in life. The downside about that is that I'm a voracious reader and consumer of data and sometimes I need to force myself to step back and just completely disconnect. Case in point, I was going to go with my friend, Jan, trekking in that same Wakhan Corridor in Afghanistan in August of 2020 because there is no radio reception whatsoever there. It's one of the few places on earth you're completely cut off.

And that allows your brain to completely rest, do a reset and really think about the hard problems in your life and where you're going. Unfortunate, it didn't happen. The big C, it's ... Yeah, what can I say?

Jeremy Au: [00:28:08] First time I heard it described as the big C. Maybe that's the new way. The year that shall not be mentioned.

John-Simon Purcell: [00:28:14] Well, that's the unfortunate thing is that's we are seeing its impact globally and lots of different places in the world, obviously in parts of Southeast Asia, I'm jealous of Ryan here who I see also in the audience in Vietnam. You guys in Singapore who have a much saner life right now than what I have here in the Netherlands. And I'm not sure when it's going to get better anytime soon.

Jeremy Au: [00:28:38] So kind of like keep going on that track around learning you're voracious reader. So you mentioned a couple of things along the way. You've been reading Ben Thompson. What else do you read?

John-Simon Purcell: [00:28:49] One of the best books that I've read in the last couple of years actually is by a friend of mine. His name is Jan Chipchase. So that's a Jan as in J-A-N like Jan. Jan is a German or Dutch for John. And that's Chipchase, C-H-I-P-C-H-A-S-E. He and I worked together at Nokia in different divisions. And so he leads global design teams into challenging and interesting parts of the world. The Afghanistans, the Nigerias, the Pakistans, DRC.

I think he's probably one of the few people I know who's been to as many places as I have, and the more interesting ones. My idea of holiday is to go to Afghanistan, climb a volcano in the democratic Republic of Congo, et cetera, et cetera, et cetera. But he actually has a book called The Field Study Handbook. It's a really fantastic resource for those interested in getting deep into the qualitative versus quantitative studies, the why's versus the how's.

Remember, we have an abundance of data. That's not inherently a bad thing, but it can really distort our worldview because it just tells us the how's. It doesn't give us the tools to explain the why's, why people are doing things in the first place.

So that's one book I've read that I've reread a couple of times. The other one would probably be The Messy Middle by Scott Belsky. Scott is actually the CPO now for Adobe through his acquisition of his company called the Behance, which is like a community for designers. And that book is great because it's just like snack-sized nuggets of knowledge for finding your way through the hardest and the most crucial parts of any kind of bold venture as you go at scaling from just getting funding at seed stage all the way up to getting acquired in his case.

And the nice thing about that book is because it's like these snack sized nuggets, it doesn't have to be read linearly. You can read like one aspect and then flip 500 pages later and look into a different aspect. And so it's a nice little reference for, "Hey, I'm facing this problem. Is there anything in here where it may describe ways of considering things?" It's much more of a mentor way of writing and making you think of ways to get yourself out of the problem. That's a great one. 

And the other one that I review probably once a year is a book called People Styles at Work and Beyond, I guess. And I think the tagline on that one is like making bad relationships good and good relationships better. And this one, again, it gets my key points before about stressing communication and culture. We all have our own communication style and some people have high EQ, or emotional intelligence. Some have relatively low ones. It doesn't mean that you're not as smart as someone else. It's just your way of communicating is different.

You have the stereotypical engineer or the beanie hat that doesn't know how to articulate themselves or understand the person who is in the go-to marketing team and vice versa. It's not because they're not both brilliant people and this is actually something I learned at MTV, is that their communication styles were different and their styles were clashing. And so the information wasn't getting across to each other.

And so this is a book that it's all about realizing your own communication style, how to identify other style and knowing when to change your style to prevent those communication classes and knowledge loss. And so it's something I routinely remind myself of that, do I know how I communicate? And when I meet people, I can instantly pick up on, or in most cases, pick up how their communication style is. And again, the only thing I can control is my own self and my own behaviors. And so I adjust my communication style to match theirs because I can't assume that they're going to do vice versa. That's a really, really great book. I really want to stress that one.

That being said, understanding people's communication styles can be difficult in the Zoom world because for a lot of people, communication was massively impacted by nonverbal communication. You guys in Asia understand this, high context languages such as the various Sino dialects, Japanese, Korean super high context. And it's really about what's not said versus what is said, and contrast that to dramatic languages like German which is super low context, which means that if it's not verbally said, it just doesn't exist.

And there's an ocean in between a nuance that's really, really difficult for a lot of people now that we're in the Zoom era. And so we have to be extra cognizant of the people on the other side of the camera and give them the benefit of the doubt sometimes.

Jeremy Au: [00:33:55] It's interesting that you reviewed that book once a year. How would you say that your communication style has changed over the years?

John-Simon Purcell: [00:34:03] Again when you start your career, going back to what you said in university days, for certain careers, it's not necessarily about the amount of knowledge that you have. But it's really about tuning yourself in and the mindset that you have.

So if you look at engineering, particularly physical engineering and structural engineering, biomedical engineering where people could die and those kinds of things with slip-ups, or law, your way of approaching the problem radically changes when you go through these degree programs themselves or become one of these professions.

The issue there though is you have to remember that not everybody has gone through your same professional training or has your viewpoint on how to approach a problem. And so you see this time and time again where people put in, they don't read the room, kuuki in Japanese, or read the atmosphere itself. And they put in tons of jargon or other things in a room full of people who frankly have no idea what you're talking about. And it really plugs up the communication works and slows down getting the job done.

And so that was my issue at MTV, is that being an engineer coming out of Microsoft and all the Microsoftisms that were there, it took me a while to shake that off and realize that, "Oh, wait a minute. The vice president of go-to marketing in MTV," which came out with a brilliant campaign slogan, "I want my MTV" in the '80s, I will [inaudible] myself. But everybody in the country who was under the age of like 18 knew that slogan. It was absolutely brilliant. But us communicating together was really loggerheads because our communication styles were very, very different.

Jeremy Au: [00:35:52] Wow. That's amazing reflection there. I think what's interesting for you is obviously, you've been a strong operator and obviously, you see over your career that you've taken on one more advisory roles. And right now, you're also acting as a bridge between venture capital as well as startups. So, I'm just kind of curious, do you feel like the different skillsets that needed to succeed in these different roles they're different from each other?

John-Simon Purcell: [00:36:17] Yes. Again, it gets back to that curiosity aspect. And as you get older, the big thing that you have is that you've gained a breadth of knowledge. And you can start doing some pattern matching, and so apply things that you've learned in one domain and apply to another. And so, one of the key aspects of that though is broadening your domain knowledge so that you can start to recognize those patterns in other domains and apply it successfully, or at least suggest to someone, "Hey, I don't necessarily know if this is the answer. I've seen this pattern in another area. This sounds very much the same in your area of expertise. And you're the expert, not me. What's your take on it? Am I thinking of things incorrectly?"

A lot of what I do in certain ways almost like a bartender. I listen to people and they'll pour out stories of how they've done things in the past, how they built their product, the woes of how they built their organizations. And it's really my job to help them get through that mental block in certain ways that they're under for them to reach their maximum potential.

Jeremy Au: [00:37:35] Now that you've gotten to see and be that bridge between startups as an advisor, as well as VC as an advisor, what do you think are some common misunderstandings that happen in terms of communication styles from the founder perspective looking at VCs. And later on we'll look at the VC angle looking at founders. But what would you say are some common communication, misunderstandings that happen from founders looking at VCs?

John-Simon Purcell: [00:38:00] So I think first and foremost is that every founder, when they're trying to do a raise of a round, it either may be with one VC or better yet if you're actually a successful company, let's say you're especially going between that AB crunch or BC crunch, which in certain parts of the world can be very difficult to raise, you're going to be potentially talking with a lot of different VCs.

When it comes to communication though, I find this particularly a tragedy because I don't like to waste people's time. I don't like to waste startups time. They have better things to do than to really talk to me sometimes if we're at just this "should we invest" stage or not because they need to build a product. And then conversely, I don't like to have my time wasted either if they're really not interested.

And so, I have largely automated a lot of the questions that we have for product and tech in particular, which also covers legal aspects. Again, that company culture pieces, I've automated all that to really just be a lot of form based off that as if some of you who are on the call who have gone through it, it serves as a nice basis. So we take care of all the mundane stuff beforehand, and we can really get to the nitty-gritty of what makes your product and your company unique that we want to invest in. The unfortunate thing there about VCs is that process is not standardized whatsoever.

If you look at Y Combinator's greatest contribution to the industry is that they open source their term sheet. And so that acted as a basis for a lot of the startups, at least in the United States. And so they didn't have to like, other VCs could just take that and say, "Okay, here's the basis points. We tweak one or two aspects of it. And that's all we have to wrangle about and we can go on."

There is no equivalent of that for the entire process of gathering money from a venture capitalist, and that can be incredibly wasteful for startups. I remember once, actually it was the one I described before in 2018, as we were leaving, I overheard somebody in the office and they said to the CEO, "How many of these do we have to do again this week," in terms of talking to investors because they're all different. They all ask for different things. There's no baseline to say 80% of it is covered by everybody, which eventually it is. And then there's the 20% that may be unique to the VC's point of view as to why they should invest. And it's really bogging down the startups.

Long story short though, I would encourage all the VCs out there, especially the ones that are doing later stage checks, just be cognizant of the startup's time and resources because they're out there to build a great product, not necessarily to be constantly raising money.

Jeremy Au: [00:40:51] That's tremendous feedback and I hadn't thought about it that way. But yes, I think the SAFE note, for example, has been tremendous. And one thing I always think to myself sometimes is like the YC application form is a pretty good summary of a lot of questions that VCs are going to ask at least to get through the first stage. And there's so many different ways to ask that same set of questions over and over again.

John-Simon Purcell: [00:41:10] Exactly. And unless like you have this baseline ... And this is, maybe Ajey and I should get together and maybe talk about a product and tech due diligence for startups in the region as a talk sometime. But because everybody does it differently and it may be just a slight tweak, it takes an extra 15, 20 minutes out of somebody's time to answer this. And that starts to add up when you get sometimes hundreds or thousands of questions there.

But on the contrary, I also have to stress too, is that for the startups out there, there is no right answer to these things because we, or at least I expect, again as you go through the stages of you raising your rounds as your company gets bigger and bigger, that because you've gained more domain knowledge, you're going to throw away some of the implementations that you've done in the past like fall in love with the product. It's going to be the problem and not the solution.

And so don't also try to game the system because if you're a seed round, you're not going to have that much information to gather versus like if you're pre-IPO, this could take weeks or months. And I did this actually over Zoom this summer for a nine and a half billion dollar deal, and that was incredibly hard because it's a lot of money. And the amount of questions that you want to ask is endless. And you have 80 people on a Zoom call trying to get something done. Keep in mind, time is precious.

Jeremy Au: [00:42:38] 80-person Zoom call, trying to get something done. That's quite something. So, the question I have here, of course, is you've obviously seen a lot of startups on both sides of the table either successfully raise money or get rejected. And I'm just kind of curious for a lot of startups who get rejected along the way right in the seed stage, series A, series B. And obviously, who knows whether they managed to raise a round from another investor. But I guess, when they get rejected by a specific investor, what advice would you give them and how to think about that rejection by that one investor?

John-Simon Purcell: [00:43:14] Well, rejection in life is a tough thing and it really depends on the type of rejection. But in general in this business, especially if you're a founder, you have to have a very, very thick skin to survive in this industry. Odds are completely against you. I don't know if you can quote me or not but it's, what is it, 96% of all startups fail. Once that become a unicorn, it's like, I don't know, one in five billion or something like that.

So, you're going to have a lot of rejection along the way. The key aspect of it is how do you deal with every rejection and why is there a rejection. Sometimes, it could be that you've got the right problem but the wrong timing. I think we mentioned this the other day about Friendster. In 2002, it invented social networking but had a horrible solution and the timing was wrong for it. Fast forward five years or so, and you have Facebook, the timing was right. It took off like gangbusters and now, they're the behemoth that we have now.

So, you do have to ask yourself, "Hey, if I'm getting rejected by a whole of VCs, is my product just the wrong timing for it or am I giving it a wrong timeline?" I think Ryan actually stated this before too, is that most VCs operate on a 10-year timeframe where they understand their funding cycles. They gather money from LPs or limited partners. They have 10 years to use that money. And so around year eight, they're going to have to start making some liquidations to pay back their LPs. If you have a business idea that's going to be 15 or 20 years on the timeline, clearly, not a whole lot of VCs have that amount of runway to help you out. 

And secondly is, again, it gets back to finding the right VC for you. This is a relationship and it's a relationship that you're going to get into potentially for a number of years. So, you could get rejection from a VC primarily because they just say, "Hey, I love your idea, but we're not the right VC for you." I think the key thing there though is the VCs in the room give feedback. How do we learn? We fail, and we get feedback, and we try again. If you don't give that to the various startups themselves that you've taken the time to really set aside, listen to their pitch and those kinds of things, they're not going to learn and they're going to try the exact same thing on somebody else. So, feedback-feedback-feedback is super key.

And that's one thing that we do actually is at the end of our diligence process, we put together a document that says, "Okay, regardless of whether or not we invest, here is like x, y, and z that we've seen that this company needs help with." And we present that to them afterwards generally of just giving basic feedback of, "Hey, you know what? We're not the right investor for you. Here are some of the things that we've noticed through the process so that when you go to your next potential investor, you'll be able to work on these things or work on that message and be better for it."

Jeremy Au: [00:46:16] You shared tremendous amounts by experience and advice here. And my question is, if you could travel back in time in 10 years and you could speak to yourself then, what advice would you give yourself? Of course, it's about a content, but also how would you give that advice to yourself?

John-Simon Purcell: [00:46:33] That's a great question, and I'll answer it like this. A couple of years ago, a colleague of mine who is younger than me, he is a growth and marketing wiz that I am in complete awe of, and I learned so much from. We are in a bar in Buenos Aires, I want to say all I can remember is 2018 or 2019. He was turning 30 that night and, "Hey, you know what? We'll go out and have a few drinks and celebrate."

and he said to me this, " Looking back through your 30s, what advice would you give yourself to get through things?" And my answer was pretty plain and simple, " It will be okay. It will be okay." The reason why that is, is I mean for myself in my 30s, let's see, I had an upfront row ticket to 9/11 because I lived 75 meters below the World Trade Center, as in south of the World Trade Center on a beautiful Tuesday in September. Planes dropping on your head in terms of [inaudible] . My wife had health issues for a while there. You have career issues as well.

If you're starting families ... I do not have children, but a lot of people start having families then. They have that work-life pressure, especially for our high performing women out there. It can be a lot to take into account. And you might say to yourself, "How do I get through these all?"

my point being though is that at the end of the day, it will be okay. You'll get through it. The biggest thing to do though is ... I remember this actually vividly from a small guest house I was staying in Dakar a number of years ago. And the innkeeper would never say the goodbye to someone. He would always just say, "Stay happy."

and that really stuck with me for a number of years, and it's the same thing I'd say today, is there are no goodbyes so just stay happy. And if you're happy and mentally happy, it was tough to do and you understand that, "You know what? This is life. It's trials and tribulations. You're going to have ups and downs. You're going to have ..." Stock market goes up and suddenly, you're super rich. Stock market goes down, suddenly, you're super poor. This is life.

And that you're going to have more highs than lows, but if you mentally prepare yourself for that and be very pivotable in your outlook and view on life, you're going to be a lot stronger when the tough times come and be able to duke it out.

Jeremy Au: [00:48:57] Thank you so much, JSP. I really appreciate you sharing this 

John-Simon Purcell: [00:49:02] Thanks Jeremy

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