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Demystifying the conversations we're already here at RRE and with our portfolio companies. In each episode, your hosts, Will Porteous, Raju Rishi, and Jason Black will dive deeply into topics that are shaping the future, from satellite technology to digital health, to venture investing, and much more.
Raju: I know. But the thing is, like, I love dessert, and sometimes I’m too full by the time the meal is over. But if you eat it at the beginning—
Tricia: That’s right.
Jason: That’s true.
Raju: —it’s fine.
Will: Yeah, but dude, I’ve eaten with you for a lot of years, now, and the reason you’re so full is because you ordered all of the appetizers.
Raju: That’s true.
Jason: Every side. I will have every side: the creamed spinach and the regular spinach.
Raju: Yeah. Yeah.
Jason: All of the truffle mac and cheese, and the bacon mac and cheese.
Raju: Yeah. Well, I mean, come on, you can’t have too many sides.
Tricia: It’s about the experience. Right, Raju?
Raju: Yeah. It’s the experience, experience.
Jason: There you go.
Will: Welcome to _RRE POV_—
Raju: —a show in which we record the conversations we’re already having amongst ourselves—
Jason: —our entrepreneurs, and industry leaders for you to listen in on.
Raju: Hello, listeners. This is Raju Rishi along with my partners Jason Black and Will Porteous. Today, we are joined by a famous, infamous, dynamic, and altogether wonderful Tricia Han. Tricia has been an executive and CEO at many, many, many, many consumer tech companies, including Vindigo, Rave Wireless, DailyCandy, Dotdash, WebMD, Daily Burn, Care.com, and MyFitnessPal, most recently. She’s also on the board of several public companies, including Latch and Empire State Realty Trust. And we are luckily enough to have her as an EIR at RRE Ventures. So, welcome to the podcast, Tricia.
Tricia: Thank you for having me. Long time listener, first time caller.
Raju: [laugh].
Tricia: So [laugh] happy to be here.
Jason: There you go.
Raju: Oh, my God. So I couldn’t do your background justice. There’s just so many world‑class companies that were there. Can we just pick off your latest one, MyFitnessPal, and kind of talk a little bit about kind of the growth trajectory from when you joined to when you wind up leaving the business. I mean, it’s a tremendous success story in so many dimensions. I’d love to hear a little bit about that, and then we can frame out the rest of the discussion, which I think we’re going to take in a few counterparts—a few parts.
Tricia: It does sound like I had three careers, almost, and I even forgot how much [laugh]—how many companies are on that list. But, in terms of MyFitnessPal, it—you’re right, Raju, it’s a really special company. MyFitnessPal, for those people who may not know, is the number one fitness and nutrition tracking app in the world. There are over 200 million registered users and counting. It’s number one in its category in 50 different countries—operates in 120, and it’s probably, you know, in the top three in the other 70.
And last year, in 2023, MyFitnessPal was one of the top 20 global apps by consumer spend outside of games, and so it’s really a tremendous business. You know, when I started there, it was—it had been a business that had already been in existence for 15 years. So it is one of the original apps, and, in fact, I think it was one of the first apps that appeared in the Apple App Store, when they launched the app store way back when, which his part of what gave it some of its advantage. And, you know, I think you see that, actually, in a lot of apps—first mover in a lot of these categories have a great advantage. But what is amazing about MyFitnessPal—and, you know, I’ve talked to Will about this is a little bit.
So it is a mobile app. However, as I spent more time in the business, and as I looked, frankly, at a lot of other mobile app companies, what you start to understand is that in addition to being an app and often a utility app, there’s actually a massive data business behind all of these applications because what they’re doing is really collecting information that—I think users sometimes—they know, but they’re not necessarily mindful of: of course, geolocation being a primary one; and for something like MyFitnessPal and many others, a lot biometric data. And, granted, you are giving this data to the application as a user because there is some utility and value to you, whether it is helping you understand what you’re eating on a daily basis—which is what MyFitnessPal was about, as well as fitness in general—or a lot of FinTech apps, same thing, like, what’s happening with your money. So it’s a really interesting space, very dynamic. And I will say mobile apps are—I mean, it’s basically the internet these days.
Raju: Yeah. And I—if I look across these various companies: WebMD, Care.com, MyFitnessPal, and others; I mean, these are category leaders [laugh] across the board, man. And you’ve had the opportunity to lead them, and I am—I mean, I’m just so proud to know you. [laugh] I really am.
So let me frame the dialogue because we’re not going to just talk about consumer apps today. There is going to be a big chunk. I’m going to ask you a bunch of questions, and then my partners are going to ask a bunch of questions around, you know, just the state of consumer apps and what works and what doesn’t work and where they’re going. I also want to spend a little bit of time on female executives and CEOs and sort of what you’ve seen happen over the years, what’s different now. And then, also, Asian American executives, they’re slightly different, so I’d love to hear your thoughts on those. And then I’ll end the session—or actually, we will end the session with a bunch of fun questions, and then a gatling gun section, which if any listener has listened to, is actually the best part of the podcast.
Tricia: [laugh].
Raju: So okay. Let me just kick off the first question, and I’d love to have Jason and Will chime in. So, you know, you’ve led the who’s who of consumer companies at various stages. But let’s pick out the early ones first. The early-stage ones, you know, are there key characteristics or operating metrics that you’re looking for as an executive there?
Tricia: At early stage, it really is about the fundamentals, which means it’s really about your customer. You know, in addition to leading companies, I really came up through the product ranks. And the place I’m always going to start—I have that bias, for sure—is who is the customer. What is their pain point? What is the value prop? How can you solve that in a way that’s going to be differentiated and interesting?
And that really needs to be the basis of any of these mobile apps, early or really late, and to kind of keep that top of mind. So, when you’re looking at metrics for an early-stage company or mobile app, I think it does come down to how are you ascertaining product-market fit? What does usage look like? What’s repeat usage look like? Downloads is part of it. Is the value prop interesting enough for people to actually come check out our app? And understanding retention and churn overall. Now, monetization is important. CAC is important. But I think you get to those a little bit later. If you don’t have the basics, a product that people actually want to use, you might as well start over.
Raju: Yeah. We have some listeners that are early-stage consumer startups. Any sort of unusual tips that you would give them or ways that they can think about figuring out product‑market fit. Because there is a lot A/B testing that goes on. There’s a lot of focus groups. I don’t know how you do it. But any tips that you would give folks that are listening here that are at the early stages that they should do?
Tricia: Well, it probably is about talking to your customers in any shape or form, whether that’s direct or even indirect by looking at things like ratings and reviews. You know, I’ve met a lot of founders who are so smart, but sometimes they way they approach the market is still like, “I have a great idea. I have a great solution. Clearly, there’s somebody who wants it.” But they can figure out very quickly if that’s true or not by really spending some time with their customers.
So I think both the qual and quant here are very important. Of course, there are ways—I think there are a lot of ways to also test these things before you actually even go in and build these things. We’ve all heard of things like the fake doors, the red doors, to see if somebody would actually buy a product. I also like frameworks where you might be thinking—you need to ask yourself the question of what has to be true for this product to be successful? Meaning there are enough people who actually have this problem; there are enough people who would actually pay to solve this problem, and there aren’t a gazillion other competitors in the space who haven’t already figured out a way to address the market. When you ask those questions, you can very quickly validate a lot of your theories and plans before you even build it—you know, a line of code.
Jason: I’m kind of curious. Like, you know, obviously, like, all the early metrics and speaking to your customers makes a ton of sense. I know even in—like, applications and B2B go‑to‑markets, you can sometimes trick yourself into thinking, you know, of product‑market fit because your early customers are really excited. But that next wave, not so much. How do you kind of, like, break through that initial barrier and make sure that you’re not just building for an initial set but also for a much broader audience?
Tricia: That is such a great question. And you’re right. It’s a hard thing to figure out. And, again, you know, I just think you go straight back to your customer, and you’re watching their retention, overall, and usage. And I think one thing—and for apps in particular, understanding your daily-actives and your monthly-actives, you get a really good sense of can you—have you build something that’s sustainable over the long run, and as well as, like, thinking about who are the various segments and understating, again, that overall TAM.
Will: So, Tricia, what about beyond that? What about growth and kind of growth hacking? You’ve watched a lot of consumer brands scale to efficient acquisition models. And, to me, this is, like, a dark art that is really only understood by a select few. You are one of those select few.
Raju: And Voldemort. Voldemort also has that.
Will: Right. Voldemort had great marketing, as we know.
Raju: Yeah.
Will: Mostly fear driven. Tell us kind of what you’ve seen work in that journey of refining a growth strategy.
Tricia: Well, okay, so speaking of Voldemort and maybe [laugh]—and maybe less than some more questionable areas, like, an interesting place to look a lot of times is—that I’ve looked in the past is weirdly Las Vegas and slot machines. And I say this because, like, friction is the enemy in a lot of cases, not all cases and so I’ll get to that second part later. But a lot of what is needed here is putting yourself in that customer’s shoes, walking that journey with them, and taking out every single piece of friction in the process of introducing yourself to them in terms of getting them to sign up and in terms of then helping them understand the value prop of your product as quickly as possible. People—you know, we’ve all heard the stats. People’s attention spans have gotten shorter and shorter, and that’s absolutely true.
But even when people want to want to use your product, the minute you throw up a blocker—they might have the best intentions, but they’ll be out of there. So I’ll give you an example of this. I often see—it’s like a really silly thing, but as you ask someone to give you information about themselves so that you can better serve them, a lot of people will say, “Well, hey... give me your email address and create an account and give me a password.”
And that’s a very reasonable thing to ask. However, a lot of people weirdly struggle with coming up with passwords. And so because they can’t think of one that needs to be safe and secure, they’re like, “I’ll just come back later,” and then they don’t come back. And so you have to be really thoughtful about every single step. And so this goes back to Las Vegas and slot machines. I’ve been really interesting in understanding how they thought about it, not because I think it’s good, but there’s a lot to understand about human behavior.
Raju: Yeah.
Tricia: And when you [audio break 00:12:03] the history of that, right, they figured out how to speed up play. They figured out how to not make you get up and get change to put in the machine. They figured out how to let you play two or three machines at once.
Raju: Did you know that Jason’s grandfather, I think, invented the slot machine.
Jason: Great-grandfather, yeah [laugh].
Raju: Yeah. Yeah.
Jason: Don’t worry. None of that was passed to me—
Raju: [laugh].
Tricia: That is fascinating.
Jason: —or else I wouldn’t be on this pod. No, it was, like, the Mills family on my mom’s side. It was my great-grandfather. Yeah. There’s Mills slot machines. I actually saw them in the San Francisco Airport. They did, like, a history of slot machines or whatever. We actually have one—it was originally at my grandma’s house but now at my sister’s place.
Raju: And I think I’ve lost half my income in that machine. It doesn’t pay out.
Jason: And it’s like these old nickels because they are super old too.
Raju: It doesn’t pay out.
Jason: They have, like, the Buffalo nickels in there.
Rajul: I know. And I tried to put an entire buffalo in there, and wouldn’t fit. And this was, like, friction.
Jason: [laugh] There you go.
Tricia: Yeah.
Jason: My mom has played it for, like, her entire life, and I’ve won it, like, five times, and she’s, like, [laugh] never won the jackpot. But anyways, that’s a pretty random side quest there. But it is fascinating.
Tricia: It sounds like the equivalent of the flip phone. Right? It’s probably the gentler, safer slot machine, the one that your family invented, versus what we—
Jason: Well, it’s all mechanical.
Tricia: Exactly.
Jason: Which is super cool. But it’s the same thing in, like, you know, the NBA. Right? They invented the shot clock. Before, you didn’t have to get a shot off, and it just made it that much more engaging. Right? And it made the play more engaging.
Like, we’ve seen this across the board that, like, any point of friction—I think one of the best—I’ve been signing up for a lot of AI-related things, as many people are. I actually just bought, like, an audio pen this morning, which we’ll see how these all these, like, kind of secondary devices end up panning out, but fun to try them. But the high from inflection—it had this amazing signup flow where you just download the app, and then it just opens, and it is the chat app. And you haven’t put in any information yet, and so you just have your initial chats with it. And, like, ten messages in, it’s like, “Oh, by the way, if you want to, like, save your chats, like, could you put in your phone number?”
And you just, like, type in your phone number. And then it’s like, “Oh, okay. Great.” Like—and then it kind of comes back to you later for more stuff, but you’ve already seen what the app can do, and it was just this unbelievably seamless process, where you’re just like, “Oh, okay. Cool.” I walked in, and I got this magical little experience. If it just disappeared and I downloaded it again, I wouldn’t be upset that, like, my chats weren’t saved because I never put any information in. But if you want to, you can, like, just toss it in and save your chat history. And then eventually, you know, buy the end, you have a full account.
Will: So that sounds kind of super casual, almost fake casual, on the part of the app owners, but yet, they give you a really rich taste of what you want [audio break 00:15:03] to sign up. That’s very smart.
Jason: Yeah.
Raju: So friction everywhere except tires. You want tires.
Tricia: There are various ways you don’t want—you—it’s actually okay to introduce friction, and this is the opposite side of this. And so, as you know, I’ve spend a lot of time in health apps. I’ve also worked with financial apps. And that is actually the opposite scenario. You actually want to ask your customer more questions along the way to understand what their problem is and to help them understand that you may have a solution for them at the end of this process. So that’s—it’s like the difference of visiting your doctor versus going to Starbucks. At Starbucks, you want it to be fast. You want it to be quick. You want to get out. But your doctor you kind of wish they would spend a little more time with you.
Raju: : Hmm... that’s interesting.
Tricia: What’s your problem today? You know, have you been sleeping? What are you eating? And so, interestingly, there can be opportunities where introducing some friction actually builds trust in the relationship. And as they—if you are a entrepreneur, you need to figure out which customer are you serving or what does your product serve, and, therefore, how do you build this?
Raju: Yeah. I have a lot of trust in my marriage—ton of friction, but it’s been—but nevermind. I don’t—Patty, I love you. I love you. So let me move on to the next—
Jason: [laugh]. You better hope she doesn’t listen.
Raju: I hope she doesn’t listen to any of these. I mention her a lot. Okay. So same question, later stage-ones, you started alluding to it. You know, what are the important key characteristics, operating metrics, that you look for in later stage apps? And we’ll get on to sort of managing them later, like how you grow them and build them, because you started alluding to some of those really interesting points on growth hacking and whatnot. But just, like, what are the characteristics you’re looking for and operating metrics you’re looking for in an established app, consumer end?
Tricia: Well, you’re still looking at all the usage stats, for sure, and understanding downloads and customer sentiment around your product. But, if you’re a later-stage, you’re probably thinking, “Hey... we’d like to make some money of this someday,” so you start to think about your LTV, your CACs, your revenue, your unique economics overall.
But you have to keep a really close eye on your competitive set. So everyone knows there are a lot of apps in the app store. There are, like, two and a half million different apps in the app store, and pretty much whatever category you’re thinking, it’s not unusual that there will be 30 to 40 competitors already there. And so you also, I think, want to understand market share and sort of where the customers—where are they spending their time.
Will: Two and a half million apps, [laugh], wow. So for you, as a consumer CEO, how do you think about kind of white spaces and where opportunity may lie. Like, what are the things that you react to, and, like, what are the things that you ignore when you’re thinking about what the—where future growth or future opportunity may be?
Tricia: Well, it does feel like there’s less and less white space. But what you see, interestingly, are people jump on trends very quickly. And so, for example, in—I think in ’23 with the immergence of AI, you suddenly saw, like, thousands of apps add the word “chatbot” or “GPT” to their app descriptions, like, four or five, seven thousand of these apps. And some of the researcher is showing that this actually is very useful. And so what it speaks to is you need to continue to innovate and differentiate on the app side, and you pretty much need to shift frequently and quickly to kind of stay ahead.
And it may not be net-new, but it might be an interesting new take. And so, you know, obviously, social continue to dominate in the app stores, and this one may not be at the top, but it was interesting to see something like a BeReal come in and get some attention, given how much competition there is in the space. Or the other apps that you started to see come in last year, which is super fascinating, like the SHEINs and the Temus all of the sudden—massive downloads in many, many countries. Ecommerce is not a new concept, but there’s something that—there’s a flavor that’s got to be slightly different about what you’re doing than everybody else.
Raju: Yeah. So, Tricia, I’m going to move on to just another broader—just, like, things that are happening in consumer apps, like the broadest levels. And we’ll talk about—and if you’ve got others besides this, I’d love to, you know, sort of pick your brain on it. But one of them is how do you balance this excitement, initial excitement, to get people to download the app and then building enough capability in this thing that you have low churn and, you know, people create longevity? Because there are different feature-sets that get people to download versus get people to stay. Is that just sort of an art form, or is there some science around that?
Tricia: It’s probably a little bit of both. That’s such a great question. Hopefully, the features that keep people on the app are the same ones that get them download, you know, back to value prop and the customer. But you’re right. I mean, it’s a big problem. So I think there’s a stat out there that says something like 75 or more percent of people who open an app once do not ever come back.
And so I would say, again, what’s the value prop? What is—what value are you offering to the consumer? And you need to lead with that almost always. I think there’s a lot you can do to get people to download the app that may not be about features. It might be more about marketing. It might be partnerships or other ways to draw attention to the brand. I think there are a lot of apps that have done a really good job of this over the years, someone like a Duolingo. You know, they’ve done a really good job from a marketing perspective.
And granted, they’ve got a good product, too, but they’ve also done a lot in terms of just the awareness. And so, you know, when we talk about growth hacking, that is a big piece of it for sure. You know, again, coming from the health and wellness space, in particular, I saw some, like, crazy stats last year. It was something like a third of Gen Z, they get their health advice from TikTok. They also get their financial advice from TikTok. And so, again, it may not be about features, but it’s about making sure that you are in all those places.
Raju: Okay. I got all the questions for this podcast off of TikTok.
Tricia: Yeah [laugh].
Raju: I was just—I was listening to TikTok. I was like, “Oh, these are good questions. I’m going to ask these questions.”
Jason: Yeah. I mean, obviously, the—not that. But it is pretty amazing, like, how much of a shift away from Google it is. Like, there was kind of a period of time—now, Google, just includes Reddit at a lot of the top of the search results just because so many people would search like, “Oh, how do I fix this washer/dryer?” And then they would literally include the word “Reddit” just because they wanted Reddit posts because it’s, like, actually from people.
I think we’re seeing, like, a similar shift to TikTok, particularly for the younger generation. It’s just like, “Oh, I’ll just search on TikTok. But probably somebody has made a video of this.” And I totally get your point around the Duolingo. They go as far as, like, having you make a commitment in the app, where they’ll like, “Are you going to commit to the—like, doing a ten-day streak?” And you’re like—you have to hit a button that says “yes, I commit myself to it.” And then they, like, notify you. So they get pretty extreme, but they do get you to come back. And you have, like, some really driven people who are—
Raju: Jason and I were there, but the founder gave a talk at TED last year.
Jason: Yeah.
Raju: And it was excellent. He talked about all the little growth hacks he had and used. I won’t go into it today because we have limited time but—
Jason: I want to ask one really quickly that’s kind of related, which, you know, we never really got around to, like, you know, the early growth hacks, and then the growth-growth hacks, but somewhere in that, like, build mode, you have to put up, like, the ultimate barrier of friction, which is monetization. And I’m curious—like, I’ve actually heard from one of our portfolio company entrepreneurs that one of the regrets from building in the early days was not monetization earlier because it just highlights areas of the business that, like, allows you to quickly validate assumptions that you may assume people are willing to pay for or assume would be better than the competition, but, once you’re charging for it, it really highlights it. So I’m curious, like, when can you determine that the moment is right to turn it on? And is better to, like, put up bigger barriers and really push people, or are you doing these small tests? Like, maybe walk us through some of the early monetization experiments that you’ve seen work out and maybe not work out well.
Tricia: Yeah. I mean, this is hotly debated in all of these companies because it’s very hard to know. And, again, the market is so crowded in every single category. If you are not at the top in terms of overall users, it can be difficult to—essentially to exist. It becomes a sort of existential question.
Some of it also will depend on your ambitions as a company. I have met a lot of people, entrepreneurs who have started companies—and this is not a diss at all, but, you know, their ambition is really to have a lifestyle business, so they’re a smaller scale with some decent monetization. It works for them. That being said, I’ve also met entrepreneurs who—you know, they have really big ambitions, which also, you know, great. Not good or bad.
And they have to make a different calculus there about growth and how they’re going to get to the top of those charts fairly quickly so that they can then use that as part of their overall defense and as a way to spread—you know, for word of mouth. So to a certain extent, it depends on the entrepreneur or the team, the investors, and what they see as a potential for the business. That being said, to answer your question more directly, so, again, you know, back to stage, I think it is more important to get the user and prove the value prop fairly early on. That being said, I kind of like to hedge a little bit and, say, often be in beta mode or help the user understand that we’re going to be free for now, but that this might change. Because, as you know, there can be huge backlash when you change pricing on users, and especially when you’ve grown to a certain size.
So there is a little bit of sort of user expectation here. And you’re seeing a lot of experimentation in the market of people trying to figure this out: where to put paywalls, how and if to include advertising. There’s a lot of in-app revenue that is up for grabs too. So this requires very careful consideration based on your market, based on the competitive set. And you also kind of have to have a strong stomach for making these changes knowing that people will be upset no matter what.
Raju: Anything creative you’re seeing in the monetization front? I mean, advertising has been pretty typical. And then, you know, you got the monthly subscription. You got the in-app. Anything creative that you’re seeing like...
Tricia: Well, what you’re starting to see in the utility apps or the non-game apps is they’re starting to pull over some of those game monetization models. So, for example, like, rewarded ads. We will unlock this feature if you watch this 15-second video. That’s more standard on the game side, and now you’re starting to see it more and more in non-gaming apps. And I think as—like, we’ve all seen it in the streaming apps, for example. Right? They’re trying to have their cake and eat it too.
Raju: Yeah. Let’s shift a little bit to a big topic: privacy, security, GDPR, brand safety. I mean, it’s getting pretty crazy out there. You know, the UK, I mean, EU is kind of really cracking down on all that stuff and security. I think that Uber guy went to—like, he actually go [laugh]—like, he didn’t get a prison sentence but he was, you know, [laugh]—pretty, for, like, information leaks around users, not taking it seriously, trying to hide it. Kind of what’s the—out of the gate, like, how do you protect against that? Should founders and entrepreneurs, like, eliminate all risk from the get-go or be a little casual until they get to certain number of users, or is this sort of a non-starter now—like, you have to be, like, day one focused on it?
Tricia: That’s a good question. People do care. And obviously, there are going to be monetary damages for, you know—in Europe, you know, the gatekeepers, as they say—as much as 10 to 20 percent of their total turnover in a year. So this is pretty significant. And so, for that reason alone, I mean, it’s not great when you get called out by your customers, by the press, for having had a security breach, so I would say better not to have it.
Raju: Okay. So any other major topics in the consumer app space that we haven’t touched on that you’re kind of thinking about, Tricia, that you’re sitting and saying like, you know, this is something that entrepreneurs should know about, be aware of or kind of thinking about as they moved from stages, just anything we’ve missed? And then, you know, obviously, Will and Jason, if you got further questions. And after this section, I’ll move on to some of the other topics that we discussed at the beginning of the podcast.
Tricia: Well, one interesting opportunity for app developers are actually the anti-trust suits that are currently going on against Google and Apple, and both by the US and the EU Because what these lawsuits may result in are the opening up of the stores, and therefore, a developer’s ability to use alternate payment systems and alternate app stores. And that’s massive because, you know, today, a developer, you know, past a certain scale—you know, you’re handing, like, 30 cents on every dollar to Apple. Google has tried to get ahead of this by saying, “Oh, well, it’s only, you know, after the first million users,” or something like that. But, if you got any scale and size, it’s also a sizeable amount of money, and so that could be a real gamechanger for developers in terms of their ability to then grow their revenue. It might complicate it for them as well in a lot of ways in the sense that they have to support multiple app stores, and they may not have all the safety of Apple reviewing all their apps, but it’s certainly interesting.
So that’s one aspect of it that, you know, we’re all kind of watching and waiting and seeing what’s going to happen there. But the second thing really is, you know, back to the data and ownership of data. We are all creating so many data points pretty much every hour, and who owns that? Who gets to use it? You know, from email to geolocation to, again, all these biometrics to every message, every search, everything you buy—it’s pretty interesting to think through the power of that, the opportunity. But also, at the end, who gets paid?
Raju: Yeah. I love it. Those are really good points, and, obviously, things that people should consider as they’re building these apps. Okay. So I’m going to switch gears a bit—female executives and CEOs. You are awesome. You’ve been a leader of many, many companies and for many years, frankly. I mean, we’ve worked together for a long time.
Tricia: Yeah [laugh].
Raju: I’ve had the pleasure of working with Tricia for a long, long time, which we’ll talk about a little bit later.
Tricia: Start, were we, like, five years old? I can’t remember.
Raju: I think so.
Tricia: Yeah.
Raju: It—you know what? I think we were, like, five.
Tricia: Yeah.
Raju: It was a joint lemonade stand.
Tricia: Right.
Raju: It was—it’s like Harold and Kumar, except it was Raju and Tricia open a lemonade stand. So how has the climate for female executives and CEOs changed over time? Is it better? Is it the same, worse? What do you think?
Tricia: I mean, it’s definitely better. There are definitely more female CEOs. I heard a really funny stat last year. I think, when you look at the S&P 500 in 2023, the number of female CEOs finally surpassed the number of CEOs named John. So that’s good. But that also says, like, there’s still not that many of them in total. I want to say it’s, like, eight percent or something like that, maybe five percent globally, so it’s still relatively small.
But they’re growing, so that’s good. It’s a good trend. I will say the hard part about being a female CEO is the expectations are different for you than for your male counterparts. And I don’t think anyone is doing that maliciously. I just think that’s the nature of the beast. You tend to be under a microscope, and you kind of get dinged if your deemed to be too aggressive. But you also get dinged if you are considered to be too nice. So it’s just a—it’s a balancing act. But, overall, I would say getting better. Trend is in the right direction.
Raju: Yeah. Well, that’s why they call you the velvet hammer. Right? Is that the thing? It’s a perfect name for Tricia.
Jason: There you go.
Raju: It’s nice enough, but you still feel it.
Tricia: Yeah.
Raju: Kind of feel it. Any tips for female executives that are, you know, sort of newly into that shoe, you know, into that role, and they’re just first-time either executives or CEOs that, you know, you would say, you know, join this organization or, you know, get mentorship? Or any tips that you would give them?
Tricia: I think that’s a great way to put it. Go ask for the mentorship. There are a lot of people out there who want to see you be successful, and you need to find your advocates, that’s all—and your partners, because there are a lot of people out there who are great supporters, including RRE.
Will: Well, we appreciate you saying that, but let’s really flip the question around. What should people be doing to support women in their first outing as CEO? I think those of who want to see more women in positions of corporate leadership want to make sure we’re going the right things and not doing the wrong things.
Tricia: You know, give them the opportunity. Right? How do you hire a female CEO? You just hire one and let them learn and grow, fall down occasionally, get back up, you know, just like any other CEO. But just know that the style might be a little bit different. I think that’s the thing, you know, that—know that the way the execution happens might be ever so slightly different, but that doesn’t mean that the results are going to be less.
Jason: You talk a little bit about the progress over time, certainly in terms of quantity. Like, do you feel like you’ve been able to manage the companies, like, you know, over your history, in a different way that more reflects your kind of natural style of management rather than the one that’s imposed upon you by expectations, or not so much? Maybe the answer is no.
Tricia: No, no, no. You know, I think there is something that is—I don’t want to speak for all women or all men CEOs. You know, I can only speak for my own experience, but I do find a lot of times—and this is—and this is—you know, there’s a good and a bad to this, but women are often quite collaborative. They tend to be a little bit more contentious driven. They often are, for better or worse, sometimes a little bit more nurturing of an organization.
I actually think that works really well when you—with some of the evolving populations of employees and staff we see today, where the expectation of leadership is different: to be a bit more transparent, to be a bit more thoughtful and maybe even, again, nurturing of their careers. So I think that can be quite useful. I think there are a lot of male CEOs who absolutely exhibit that as well. So I don’t want to say, again, that this is only female CEOs. But you do—you know, there’s a tendency to be a little bit more like that as a female.
Raju: Well, that’s really helpful, and I think people will be lucky to get mentored by you, Tricia. And I say this totally sincerely.
Tricia: Thank you, Raju.
Raju: I mean, honestly.
Tricia: I appreciate that.
Raju: Yeah. No, it’s the absolute truth. Let’s switch it just slightly, climate for Asian American executives, and have you seen that change over time, or is it, you know, relatively the same? Or is there any sort of nuances or differences in terms of the way people approach those leaders?
Tricia: We’ve got some superstars right now. I mean, I’ll just say, like, Lisa Su and Jen-Hsun Huang, you’re kind of like, “woo-hoo.” You know, and not even to mention, like, Sundar or Staya Nadella. So you’ve got a lot of great role models out there right now. Raju, what do you think?
Raju: I agree. I think we’re kind of ruling the world. I think it’s a numbers game, though. Right? Like, I think there’s, like, several billion of us. [laugh] I mean, it’s just, like, you figure, like, just we’re going to trickle up to the top. I mean, it’s just a raw numbers game. Anyway, yeah, I think you’re right. I think that isn’t as much of a, I guess, discrepancy, than I think female executives. I think there’s a little bit, you know, sort of a—we need to change the game a little bit.
Tricia: Well, now, you know what? It’ll be great to see more of everyone in all of these spots because that is—
Jason: Here. Here.
Tricia: —how you get to creativity and innovation. I mean, that’s why, whenever we talk about where talent is in the world, obviously, there are other parts of the world that are really good at so many things. But when you want creativity, innovation, you come to the US because this is where you have the most interesting thinkers all rubbing up against each other with very different backgrounds and experiences coming up and dreaming up with, like, crazy things that really are the future.
Raju: Okay. Any other sort of really sort of serious questions for Tricia before we move to the more fun part of the dialogue?
Jason: Raju, you’ve been dying for this section the whole time.
Raju: I’d like to start with this. You know, sometimes I go to restaurants and I start with dessert. It is fantastic.
Jason: Do you end with dessert? Again, you just punctuate it, like, the question mark, upside-down question mark kind of thing?
Raju: No, I just go home after this.
Jason: On both ends?
Raju: I just eat—go there for dessert, and I just go home.
Jason: Okay. Dessert, dinner, dessert.
Raju: Yeah. Or just dessert, dessert.
Tricia: Like, dessert before and after?
Raju: Yeah.
Tricia: Maybe in the middle too?
Jason: See, sometimes I’ll get another main for dessert.
Raju: No, I know. You eat like a crazy man.
Jason: I like the mains. I’d rather have, like, another, you know, like, sushi course than, you know, a tiramisu.
Raju: I know. But the thing is, like, I love dessert, and sometimes I’m too full by the time the meal is over. But if you eat it at the beginning—
Tricia: That’s right.
Jason: That’s true.
Raju: —it’s fine.
Will: Yeah, but dude, I’ve eaten with you for a lot of years, now, and the reason you’re so full is because you ordered all of the appetizers.
Raju: That’s true.
Jason: Every side. I will have every side: the creamed spinach and the regular spinach.
Raju: Yeah. Yeah.
Jason: All of the truffle mac and cheese, and the bacon mac and cheese.
Raju: Yeah. Well, I mean, come on, you can’t have too many sides.
Tricia: It’s about the experience. Right, Raju?
Raju: Yeah. It’s the experience, experience.
Jason: There you go. All right. Well, we’re well and truly in the fun section.
Raju: We’re in the fun section. So I met Tricia at Rave Wireless, and this was many years ago, when we were four, right after lemonade stand, and [laugh] it’s kind of a mafia out there, Tricia. We have a lot of our executives becoming leaders in the New York City ecosystem. You’re certainly one. We’ve got Rodger Desai who is now founder and CEO of Prove. We’ve got Dan Rosenberg, CEO of Octane11; Kai Bond, general partner at Courtside; Nobu Nakaguchi, who was the founder of Zola; Ted Sullivan, founder and CEO of GameChanger. I’m leaving so many off the list. I think it was a little bit of a mafia out there back then, you know, just like—
Tricia: Right?
Raju: So what do you think it was? I mean, it was the early days of New York. New York was sort of just budding as an ecosystem, I think, in terms of startups. It just a concentration of people at certain companies, like Vindigo and Rave and others or...
Tricia: Raju, I think it was because you fed us so well. You ordered everything off the menu, and so we were just, like, energized and ready to go.
Raju: Bill Homer says—so I used to go to this restaurant called Mustang Harry’s. You remember that, Tricia?
Tricia: Yes. Of course. How could I forget?
Jason: Jesus, what a name. Mustang Harry’s? Love that.
Raju: Yeah. And so I would go in there, and I would say—I would order a hamburger as an appetizer, and I would cut it into quarters, and everybody—like, I’d order two hamburgers with eight people. Everybody get a quarter of a hamburger. And Bill Homer, still to this day, says to me, “I’m going to know that it’s not like a body snatcher if I go to Mustang Harry’s and see what you do when you order a hamburger.”
Tricia: [laugh].
Raju: If you cut it into quarters, I know it’s really you. Otherwise, body snatching. And so...
Tricia: That’s hysterical.
Raju: Yeah.
Tricia: Wait. In all seriousness, I actually do want to answer your question real quick, Raju.
Raju: Yeah. Yeah, please.
Tricia: So—because I have thought about this. Like you and like many others—especially in that crew—I actually did have a lot of opportunities and offers to go west at that time, to Seattle, to San Francisco. But I will say, for the people who are here, we were early in terms of the tech scene in New York, and we loved New York. Again, back to this—the diversity of people and thought and industry. And we knew it was going to come here, and we knew we needed to build it ourselves because it wasn’t here yet, and it was just a matter of time. And if we all—I think what you saw was a lot of people being like, “Okay, fine. We will go and just build it. We’ll go build our own companies.”
Raju: Yeah.
Tricia: And so you’ve got kind of that spirit, which is very New York in a lot of ways too.
Raju: Yeah. And I left Andrew Figenson off the list. I can’t leave Andrew Figenson off the list.
Tricia: Right. Figie.
Raju: Figie is awesome. But everyone—there’s a lot of really good people there. So anyway—and you worked with this crazy guy, Raju Rishi. I mean, what was it like?
Tricia: [laugh].
Raju: And feel free to answer this in the most positive way possible, even if you have to stretch the truth—no, don’t answer this question.
Tricia: He was—
Raju: So, no, no, no. You don’t have to say—
Tricia: —smartest...
Raju: Okay. Fine. Keep going.
Tricia: Yeah. Great sense of humor.
Raju: I know. Okay.
Tricia: But...
Raju: That’s good enough. That’s good enough. You are literally married to a rock star. Like, she’s literally married to a rock star.
Jason: Yeah. I forgot about that.
Raju: So just give our listeners a little bit. Like, what’s that like, and do you have any fun stories you can share? And where or, like, how do I become a groupie? Does he have groupies? Are you nervous about it?
Tricia: I’m trying to think of a story I can share [laugh].
Raju: Oh, that’s how good they are, listeners.
Tricia: Yeah.
Raju: This is how good they are.
Tricia: What I’ll say for work. Ugh, I’m not prepared for this one, Raju.
Raju: Okay, fine. Okay, fine.
Tricia: I might have one. I’ll think of one.
Raju: Yeah. Yeah, yeah. We’ll move to the gatling gun section, and you can come back to the rock star question because she literally is married to a rock star. He’s actually a folk star, now, I think.
Tricia: Yes. A great Country, Americana, yeah.
Raju: Yeah. And he does [crosstalk 00:41:52] for, like, legit—like, he was big in Japan. Right? He was, like, a Japanese rock star, or no?
Tricia: I think more Australia and New Zealand.
Raju: Australia.
Tricia: And also Berlin.
Raju: Berlin?
Tricia: Yes. And [he would say 00:42:03]—they like—they liked them a lot there.
Raju: Oh, my God. Okay. We’re going to come back to that question.
Jason: What a smattering, yeah.
Raju: I’m not going to leave this one alone because you got to think about it. So this is the gatling gun section. These are sort of one-word answers, two-word, one-sentence answers kind of thing. You know, we can all chime in guys and gals. Your favorite consumer app?
Tricia: That’s such a hard one. Okay. So I’m going to go really old-school with this.
Raju: Okay.
Tricia: I lot of what I like are actually utilities overall, but I’m going to go back to Dots, if you remember that game.
Raju: Okay, fine.
Tricia: It’s a classic. It’s simple. It’s really fun.
Jason: It is really fun. Do you still play it?
Tricia: Yeah. Sometimes I do.
Raju: Jason? Will?
Will: It came right out of the Betaworks portfolio, an RRE company.
Jason: Yeah.
Tricia: There you go. That’s a good one.
Raju: I’m going to say Uber because of the utility it offers me, but I’m going to let Will and Jason give theirs as well.
Jason: I don’t know. I got to go fun, and I’m going to go Reddit.
Raju: Okay, fine. And Will?
Will: Yeah. I’m an old-school answer, too, which is Instagram, just for the escapism of it all.
Raju: Fantastic. All right. Least favorite consumer app or most hated, whichever one you want? I’m going to go first. I’ve already thought about these.
Jason: Go ahead, Raju. You have the benefit of always, like, having thought about the gatling guns before everybody else.
Raju: Correct. Correct. Correct. It’s—I love that, that’s what—it’s power. I’m going to go with the why-things app, which is MyScale because it annoys me when I—I was like, “What? But I just had three desserts and two hamburgers and an appetizer. Like, why am I gaining?” I mean, [sigh]...
Will: So I’m going to go with Google Authenticator because it’s a total lurker in my life, and, like, it pops up when I need to do something, and I feel like it’s always hanging out there in the background waiting to make things more complicated for me.
Jason: I’m going iMessage—just profoundly underdeveloped relative to what is possible in the messaging space and, like, zero reason. Like, it’s 2007 introduction to the iPhone. We’re in 2024. There’s been ample time to make a baller messaging app. And by the way, just go ahead and steal and copy and do all that stuff to all the better ones out there.
Will: You are so right, Jason.
Jason: But, boy howdy, it is, like, one of the most important applications that everybody uses and almost universally hates.
Will: Totally right.
Raju: And Tricia, what’s your least favorite?
Tricia: All right. I don't like to trash other apps, being in the business. So I will just say I really get annoyed with the flashlight on my app because it keeps going off [laugh].
Raju: [laugh].
Tricia: I can never figure out how to turn that thing off, on.
Raju: Okay. All right. So now just a shift. Most used consumer app? Which one do you use most?
Jason: You keep saying consumer app. I guess I can’t pick any of the work ones—
Raju: Well, just app. Just app. Just app.
Jason: —but, obviously, my emails like super human.
Will: Okay. Yeah, so let’s throw out mail—
Jason: Easly.
Will: —and messaging out in this conversation.
Raju: Okay. Mail and messaging.
Jason: Right. Okay. Mail and messaging. Most used?
Raju: We’ll just say “find my shit” app. Find my lost shit app. I’m always losing my damn phone, and it’s like, [sigh] where is it? But I have a find my stuff app now.
Jason: Yeah.
Raju: But I don’t use that one the most. But, like, social networking probably is mine, the one I use most.
Jason: Yeah. I’d probably say maybe my podcast player.
Raju: Yeah.
Jason: I listen to a lot of podcasts. Overcast, great podcast app.
Tricia: I am a news junkie, so I probably open up, like, you know, my New York Times, Wall Street Journal—
Raju: Yeah.
Tricia: —you know, all of those pretty much every day.
Jason: Have you found any good readers? Like, all the good readers have gone away, and Feedly is terrible.
Tricia: Not really. I still sometimes will even revert back to Pocket.
Jason: Oh, yeah.
Tricia: That’s not quite proactive, but...
Raju: Okay. Another one. Tricia, have you ever made a TikTok?
Tricia: I—under duress, yes.
Raju: Okay. Fantastic. With your daughter?
Tricia: Yep. Yep.
Raju: With your daughter.
Tricia: Sure.
Raju: Okay. And what music did you use for it?
Tricia: You know, it was back in the Harlem Shake days. Remember that?
Raju: Yeah, yeah, yeah.
Tricia: Yeah.
Jason: [laugh] Oh, classic internet trend.
Tricia: Exactly.
Raju: Fantastic.
Jason: Incredible.
Raju: And Jason, TikTok?
Jason: I think I’ve made some. I made some for Misha, my girlfriend.
Raju: Okay. Okay. Fine.
Jason: So, yeah, let’s say yes.
Will: Sadly, no. I’ve missed out.
Raju: Yeah. Yeah, me too. I’ve not done it.
Tricia: Not too late. We can do one right now.
Raju: No, I know we can do one right now. I want to make one of those dancing ones, where we’re all in coordination. That would be really cool. Okay. So Vindigo, Vindigo allowed you to find places to eat, shop, and play in your local area. This is actually a cool idea, practically.
I mean, I got to be—it’s ahead of the curve. We had location-based services. It’s, like, these mobile apps were coming out. And Tricia is like—at Vindigo, we poached her from there. We poached her at Rave Wireless from Vindigo, which was, you know, a cool company. I loved the founders there. Were there any venues there that allowed you to do all three concurrently: eat, shop, and play at the same time?
Tricia: Eat, shop, and play. I do not remember but good memory, Raju. I don’t remember.
Raju: Yeah. Okay. I think there should be one, like a hotdog eating contest. You could eat. It’s like play.
Jason: I feel like that’s what Disney World is.
Raju: But then you have to buy new pants, like, because you’re so full.
Tricia: [laugh].
Jason: Raju, you’re buying the Mickey Mouse shirt.
Raju: Yes.
Jason: Like, as the fam is picking up—
Raju: Disney World.
Jason: —like, those Dippin’ Dots, and the kids are on a Mickey Mouse ride.
Raju: Okay. Yeah.
Tricia: You know what it probably was? It was probably—this will not be a satisfying answer, but it was probably the movies.
Raju: Oh, yeah. Yeah.
Tricia: That you could, yeah—
Raju: Yeah.
Tricia: —that’s where you could eat, shop for candy, I guess.
Raju: Fantastic. Fantastic.
Tricia: And play.
Raju: Okay. I’m going to move—well, what do you think of Loompa as a name for a consumer app?
Jason: [laugh] Geez.
Tricia: [laugh].
Jason: These gatling gun questions—we got to pre-screen these, man.
Will: Is this for a certain demographic, say—
Raju: No, no. No.
Tricia: No.
Will: —Oompa Loomas, you know, at large?
Jason: We got to pre-screen these.
Raju: It was actually the name of a product at Rave.
Jason: Is that actually.
Tricia: Loompa.
Raju: Remember Loompa?
Jason: Loompa?
Tricia: I don’t remember that one.
Raju: Oh, Tricia, I was expecting you to remember that. It was actually the name of an app that we developed. It’s called Loompa.
Jason: Just the original Wonka film came out, and you guys were like...
Raju: Yeah.
Jason: Incredible.
Raju: Yeah.
Tricia: It’s sort of cute.
Raju: Yeah. It’s a little cute. We didn’t launch with it. But, anyway, okay. Health and fitness gatling gun questions. Favorite exercise equipment?
Tricia: Well, I’m a runner, so, you know, it really comes down to shoes. But I also really like my head lamp.
Jason: Hmm...
Raju: Oh, that’s cool.
Jason: Some night running.
Tricia: Yeah.
Raju: Will?
Will: Yeah. Either my bike or my shoes, one of the two.
Raju: Jason’s has got to be bike.
Jason: You know. You know. It’s a bike.
Raju: Oh, my God, the guy is, like—
Jason: I’m about to go on a bike ride after this, actually.
Raju: Yeah. Yeah. In fact, he’s bike riding right now. People don’t know. It’s like...
Jason: I’m, yeah... I know. We’re a little over. I’m, like, ready to get outside. It’s beautiful.
Raju: Least favorite exercise equipment?
Tricia: Oh, the band—oh, no, the sliders. Ugh. Those are the worst.
Raju: [sigh] Uhg...
Jason: The ab sliders? Is that what you’re talking about?
Tricia: It’s so hard. Yeah. Just anything where you, you know, you put your feet on them, and you have to, like, slide up and down.
Jason: Yeah.
Raju: Yeah. Okay. And Will, you have one?
Jason: I did a neck workout once.
Will: Maybe my pull-up bar.
Raju: Pull-up bar. Okay. Fair.
Jason: Hmm... pull-up bar.
Raju: I like the pull-up bar. I don’t like the stair climber.
Will: [laugh].
Raju: I don’t like the stair climber. Favorite fitness movie? I’ll give you two choices if you can’t think of one.
Tricia: Spaceballs.
Raju: No, that’s not Spaceballs. That’s always...
Will: That was a different episode of RRE POV, but thank you.
Raju: The same—that’s always, always a valid answer to gatling gun. Spaceballs. I’ll let you think for a second.
Tricia: All right. Fitness movie?
Raju: Or, like, fitness-oriented movie. I’ve got two that I was going to toss between: Chariots of Fire—
Tricia: Good one.
Raju: —and Dodgeball. If you can dodge a wrench, you can dodge a ball.
Tricia: Is that considered fitness, dodgeball?
Raju: Well, yeah.
Jason: Absolutely. If Ben Stiller in tights—yeah...
Tricia: I was a very good dodgeball player. I did pretty good. So, I mean, you’ll remember, that Raju.
Raju: That was great movie.
Tricia: That was a great movie.
Raju: Yeah. Okay. When you were running these health and fitness apps, did you secretly keep a stash of Krispy Kreme donuts and Fun Dip in your office?
Tricia: [laugh]. Yes.
Raju: Okay. Fantastic.
Tricia: In moderation. It’s all about moderation.
Raju: Oh, okay. Fine.
Tricia: To enjoy life.
Raju: All right. Last question. Last question. Favorite candy?
Tricia: Favorite candy...
Raju: She’s, like, a health and fitness guru, and we’re asking about candy. She’s having a tough time. You don’t have candy? You don’t like candy? HI-CHEWs is my favorite, HI-CHEW. I love the little...
Jason: Oh, nice. Yeah.
Raju: Yeah.
Jason: HI-CHEWs are good.
Tricia: I love gummy bears.
Raju: Okay. There you go. Gummy Bears. Will Porteous?
Jason: I like the sour straws.
Raju: Oh, sour straws, Jason.
Jason: Sour straws. I love sour straws.
Raju: Will Porteous?
Will: Really good chocolate. That’s all I need.
Raju: Okay. Fantastic. Fantastic. Oh, this was a fantastic episode. Any rock star story? You have any rock star story before we close out? It’s okay if you don’t.
Tricia: I’ll leave that for another day.
Raju: Okay, fine. We’ll do a whole podcast on rock star stories.
Tricia: That sounds good.
Raju: All right.
Jason: Thanks for coming, Tricia.
Raju: I’ll let one of you guys close it out.
Jason: I’m doing the wrap. My wrap is simple. That’s a warp. Click [laugh].
Raju: [laugh].
Jason: Follow us on all the regular socials. If you’re listening this far, you’re already a huge fan, and I bet you [laugh] are already following us on X/Twitter @RRE, and you can find us RRE Ventures on LinkedIn. Please write in if you’re enjoying the pod. You can find our emails on our website, which is rre.com. Talk to you guys next time.
Will: Thank you for listening to _RRE POV_.
Raju: You can keep up with the latest on the podcast at [@RRE](https://twitter.com/RRE) on Twitter—or shall I say X—
Jason: —or [rre.com](https://rre.com), and on Apple Podcasts, Spotify, Google Podcasts—
Raju: —or wherever fine podcasts are distributed. We’ll see you next time.