“BetterHelp customers sign up for therapy from licensed professionals, with subscriptions up to four hundred dollars per month. But according to customer accounts and online reviews, some therapists have been secretly using AI-generated messages instead of providing real human engagement. In some cases, therapists allegedly copied and pasted AI-generated responses during live chat therapy sessions. In others, patients messaging their therapists outside of live sessions received long, robotic messages that bore the hallmarks of ChatGPT.”

“Former therapists say they are forced to overload their schedules to make a living, sometimes handling 60-plus patients per week. Many work back-to-back 30-minute sessions—shorter than the industry standard 45 to 50 minutes—leaving no time to thoughtfully respond to 24/7 patient messages. BetterHelp doesn't pay therapists for overly short or overly long responses, leading to a sweet spot where AI-generated messages are particularly effective for gaming the system.”

Blue Orca Capital’s allegations against BetterHelp and highlights growing tensions in tech-enabled labor platforms. BetterHelp is accused of using AI to replace human therapists, driven by cost pressures and incentive structures. The case reflects broader risks as AI begins to reshape trust, quality, and business models in two-sided marketplaces.

“You don't have to have management structures be purely control systems—they can be focused on empowerment systems as well. I think the assumption that most people make is that management structures are purely control structures, which is that the CEO, or the minister, or the Perm Sec, or whoever has a thing they want, and they tell the director, who tells people, and everyone's job is just to unlock. It's a massive control structure in order to do what the boss wants you to do. But as you know for yourself in VCs, yes, you need a little bit of that. But sometimes what you actually want is an empowerment structure.” - Li Hongyi, director of Open Government Products 

“The concept of ‘put in where you're parking and pay money’ is a very simple concept. It's not a big idea. In fact, I think everybody who's ever used a paper coupon is like, ‘Why you make me do this? Why can't I just use my phone?’ The idea is not hard. The difficulty was getting all the stakeholders to want to do this and to integrate with all of the enforcement systems to actually make it happen. Just to give you a sense of scale—building the actual software for the app probably took two, at most three months, at least for the first build. We obviously iterated on it since then. But the real challenge was realizing that for most of the parking lots, we didn't actually have digital records of how much they cost.” - Li Hongyi, director of Open Government Products 

“My first experience with a really good boss—not that my other bosses were bad—but the first time I really felt like, ‘Wow, I learned a lot,’ was with my manager on the search team, Peter Lindsley. He was the PM on Image Search when I was there. I remember when I was looking around within Google and talking to different people, I spoke to him and he was just really excited about all the things we could do. When you talk to other people, they’d say, ‘Oh, why are you interested in this?’ and you’d give some ideas, share some thoughts, try to solve the problem like a student putting on their puzzle-solving brain. But with Peter, I remember talking to him and saying things like, ‘Oh yeah, for image search, we could put a big map at the top of the page when someone searches for a place.’” - Li Hongyi, director of Open Government Products

Jeremy Au sits down with Li Hongyi, director of Open Government Products, to explore his journey from aspiring physicist to building digital tools for public service. They discuss agency, leadership, and the realities of driving change in government—from the impact of a Google internship to lessons in management and building systems that protect against fraud.

“And the first big responsibility I had was I was put on the team that built the first time Apple changed its processor. Now, Apple’s changed its processor multiple times—the latest being the Apple Silicon we’re all aware of. This was the shift from the Motorola 68K to the PowerPC processor, and I was part of that team. That’s actually how I ended up coming to Singapore, because we were going out and telling developers about this globally. So, first time I came to Singapore was just around the time the North-South Line opened up. That’s when I met my friend Raymond, who for the next—what, almost 20 years—kept saying, ‘Jordan, you should come to Singapore.’ And we stayed in touch. Raymond was a local developer here in Singapore; I supported him over time. And then, from there, things moved in ’99. So I was there, actually, the night Steve Jobs came back in ’96. It was a very interesting and fun event.” - Jordan Dea-Mattson, Veteran Tech Leader

“The most important lesson I ever learned from Steve Jobs—and that’s the power of saying no. Because saying no lets you focus, and focus lets you do great things. When Steve came back, the product line was just this nightmare—hardware products, niches, and everything. And Steve just went and sliced right through it to a model they have today, which is: good, better, best. You look at the product line—there’s always a good, better, best. A very simple approach. And it really makes it easy for people to understand what they should pick.” - Jordan Dea-Mattson, Veteran Tech Leader

“In ’96, Apple was on the ropes. Earlier that year, there had been ‘Death of an American Icon’—the Black Apple cover on Businessweek. And it was scary. Apple was within, I think, 90 days of running out of cash. The technical strategy—there had been this thing called Copeland—there had been all these different strategies, and none of them were yielding fruit. None of them were working. And so the decision was made: Gil Amelio, who had come in as the CEO, and Ellen Hancock, who was the CTO, decided, ‘We’re going to go buy a new operating system.’” - Jordan Dea-Mattson, Veteran Tech Leader

Jordan Dea-Mattson, a veteran tech leader, and Jeremy Au discussed how Jordan built developer tools at Apple and went on to lead engineering teams at Adobe and Indeed. They explored how he witnessed Apple’s transformation under Steve Jobs, the often unseen dynamics behind major tech layoffs, and what it takes to grow and scale high-performing teams in Southeast Asia. Jordan also shared how he led the rapid expansion of Indeed Singapore, navigated its unexpected closure, and helped his team transition. He also opens up about overcoming personal trauma, leading with integrity, and why real bravery means acting in the face of fear.

“I will say, with Indonesia, I really have faith in the people—because not only can they still create a living and make the economy run (MSMEs are the lifeblood of this economy too), but also, we are the type of people that can go against dictatorships. We can push back against things. We're known for it. Due to a viral online situation, we stopped the previous president's son from running for governor, right? So we can do things, actually.” - Gita Sjahrir, Head of Investment at BNI Ventures

“Just in order to bring everybody down to zero and make everybody go, ‘Hey, oh shoot, we're here now. We're back down to zero. Maybe we should start working together.’ And I think that's a really big issue here—lots of people not working together, lots of misunderstanding, lack of communication, lack of dialogue, and just constant assumptions about the other side—whatever the other side is, right? Public, private, pro-this political party, pro-that political party. And I think that, in the end, causes that much chaos over time. So you're right—macros-wise, we haven't really changed. Fundamentally speaking, we're actually still quite strong. But again, we need to just have more consistent and cooperative dialogue with each other, spanning the different factions and the different interests, and really be sure that we're still in a nation-building phase.” - Gita Sjahrir, Head of Investment at BNI Ventures

“We've had the high-speed rails, we've built toll roads—it's not like we cannot build infrastructure. But you're right, I think one of the ways is to keep things tight, to make sure there are not too many players, like too many hands in the game, right? But I would say, every time people get so upset about Indonesia, I will say, you know, like the leaders or the government or administration or whatever it is—you might be upset at them. But I'm actually extremely bullish, and I'm still bullish until today, on Indonesian people.” - Gita Sjahrir, Head of Investment at BNI Ventures

Gita Sjahrir, Senior Advisor at TBS Energi Utama, and Jeremy Au discussed Indonesia’s current macroeconomic conditions and policy landscape. They analyzed how inconsistent government communication, executional shortcomings, and short-term policymaking have contributed to uncertainty among investors and the public. They also explored infrastructure priorities, the structural incentives behind recent decisions, and the enduring resilience of Indonesian citizens and micro, small, and medium enterprises (MSMEs).

“Great founders get to pick, and VCs have to differentiate, right? So great founders will say, ‘I’m looking for a VC that I have good personal chemistry with, sector experience, and someone who’s fast to give me the money.’ Speed matters. VCs, on the other hand, often think founders care most about the VC’s brand—whether it’s a big name like Andreessen Horowitz or Y Combinator. They still rank personal chemistry second, and speed third. So there’s a bit of a mismatch in priorities. For me, I think speed and cash are probably number one. If you're a founder and you raise money from a VC who gives you a $5 million check today, and no one else is bidding yet, and that check expires in one week—I think most founders will take that check.”- Jeremy Au, Host of BRAVE Southeast Asia Tech Podcast

“Selling to customers is really key—because if I have a hundred dollars, I’d rather earn a million dollars from my customers who’ll keep paying me, just by delivering the product, than take a million dollars from Jeremy in exchange for 20 percent of my company. Most founders under-allocate their time to building customer revenue and spend too much time chasing fundraising. The second point is that not all VC investors are the same. There are different tiers—some are really good, some are good but difficult, and some are not good at all. Worse, some will destroy value if you let them onto your cap table. It’s easier to get married and divorced than it is to bring in an investor and try to get them out.”- Jeremy Au, Host of BRAVE Southeast Asia Tech Podcast

“When someone says your idea doesn’t really make sense, that’s actually a good opportunity—it’s useful feedback you can use to improve how you articulate the future you believe in. Take Replica, for example. It’s an AI companion for lonely people. The founder believes that everyone will have their own AI best friend. Whether or not you agree, what stood out was how clearly she explained her logic. That’s what makes a pitch interesting—it’s not about everyone agreeing, it’s about making the future you envision easy to understand.”- Jeremy Au, Host of BRAVE Southeast Asia Tech Podcast

Jeremy Au discussed how pitching, trust, and fundraising work. He explained that pitching is about expressing a future others can believe in, not just raising money. He shared how traction builds trust, why capital must be chosen carefully, and how great founders turn investor interest into leverage. Drawing on examples like Rewind.ai and BenchSci, he laid out what separates good pitches from great businesses.

"It's about right timing, in the right place at the right time. But at the moment, we have about 15 startup houses around the world, and we're very active at the moment in South America. So we're doing a lot of programs in Argentina, and Chile, and Uruguay, and Brazil. And we're also very active in India—so we have two of our big startup houses: in Bangalore, which is like the tech hub of India, and Hyderabad, which is like the second tech hub. So we're very active there. And we just launched something in Korea. It's a great area, and I think that shows a lot of promise." - Vikram Bharati, founder of Draper Startup House

"And specific topics like math and science—I think a lot of those things are going to change. And I think their ability to... I think context is going to be very important—for them to put the world into a context and have a unique perspective. And I think this is happening today. You and I, and most people in the world, have access to the same information. So the input is pretty much the same. Everyone knows everything. And so the ability to have a unique perspective is going to be the key challenge. And so how do you have a unique perspective when we're all reading the same thing, watching the same thing, listening to the same thing, experiencing the same thing? And I think that's going to be the critical thing—at least for my kids." - Vikram Bharati, founder of Draper Startup House

"It's going to provide a lot more options to people. Yeah, you know—why can't there be a digital country where you say, 'Oh, incorporate your company in this digital country,' right? And now, that digital country is surely not recognized by other physical countries today. But is it possible in the future there'll be some sort of a recognition method by other countries to say, 'Oh, we're doing a trade agreement with this digital country—they have great mindshare, and they're providing us with scientific IP for curing cancer,' as an example. And we're selling them rice and bananas in return. I think that might happen. The possibility of that doesn't seem so weird to me." - Vikram Bharati, founder of Draper Startup House

Vikram Bharati, founder of Draper Startup House, and Jeremy Au talked about how the startup world has shifted since their last conversation. They explored how Draper Startup House has expanded across continents while wrestling with the challenge of scaling both physical spaces and community-driven programming. They discussed how remote and hybrid work are evolving post-pandemic, and how startups are adapting faster than large corporations. They also reflected on parenting and preparing the next generation for a fast-changing world, where original thinking and adaptability may matter more than credentials. Vikram also shared his growing interest in “digital nations,” a concept that could reshape how governments serve people and how individuals relate to borders and institutions.

“One is, of course, AI. And I think it's a really interesting topic. I had a friend tell me—AI doesn't need a career path, AI doesn't need a weekend off, AI doesn't need compliments, and AI is a fraction of the cost of an analyst. So why do I need an analyst? And there's quite a lot of truth to some of those statements. That’s an interesting topic to explore a little bit—like if a lot of entry-level jobs were really around research, slide prep, meeting prep, all that sort of stuff, what does it mean when your partner at a consulting firm, MD, VP at an investment bank—all the way down the line—can basically have those job functions done with the press of a button, at a much lower cost and faster?” - Shiyan Koh, Managing Partner of Hustle Fund

“How do I take this and turn my interests, my passions, into a career? And maybe you start out and you're like, okay, I'm like a PT. But then there’s people who are like, "Oh, then I build a gym." "I build software for my gym." I think there’s this sort of more, like, entrepreneurial way to think about it—versus it’s not like a top-down thing. There’s this notion of, "Hey, we should actually all become attuned to what our market needs that match up with our passions." And how do we have the agency to identify those and say, let’s go try something and do it?” - Shiyan Koh, Managing Partner of Hustle Fund

“Whatever we think of AI today is going to be way more capable in ten years. We're just going to assume that you're going to figure out how to use it. And how do you, like, get them oriented towards a goal? The third one is, like, a little bit harder, which is—like—the people who can best use AI are actually the people who have the most context. Because they can direct it more effectively. And maybe the answer is—you don’t pick. You just have to be really good at learning something so that wherever you end up, you’re really good at teaching yourself how to get deep in that thing—or deep enough that you can go direct it.” - Shiyan Koh, Managing Partner of Hustle Fund

Shiyan Koh, Managing Partner of Hustle Fund, and Jeremy Au explored the growing challenges of youth unemployment in Singapore and how AI is fundamentally changing the job market. They discussed how the rise of automation is making entry-level roles less necessary, leading companies to prioritize experienced hires who can work with AI rather than train fresh graduates. They also examine how AI amplifies the gap between high and low performers, making adaptability and self-motivation more crucial than ever. They also talked about the need for educational reforms that focus on problem-solving and real-world applications, as well as how young professionals can position themselves for success in an AI-driven economy.

"You're going to make a decision. You're going to meet about a thousand—maybe five thousand—companies in a year, then decide to invest in ten of them. Think about it. You're basically meeting everybody for half an hour or one hour, and you have to make decisions fast. The reason VCs make so many decisions is that the best founders move very quickly—they’re aggressive in how they approach business. And you need to be in a rush. You need to work fast to get the deal. I'll give you an example—today, I had a call at 8 a.m., and by 7 p.m., we made a decision. We finalized it by 8 p.m.—12 hours. We sent a WhatsApp in that time, but it wasn’t enough. Now we have to fight for allocation. And I remember waiting, thinking, ‘Shit, this is too slow.’ Even I felt it was too slow. But the other way to look at it is that we could have been overloaded or just overconfident, right?"

"There was this team that met through Antler, and it turned out that their co-founder was not who he claimed to be—he had a criminal record. Imagine that—the two co-founders met this guy, didn’t know his background, and now, even though their company is doing pretty well, they had no idea that one of them was a criminal. As a VC, if I knew you had a criminal record, I’d be like, ‘No way, man, I’m not putting money into this company.’ But I’m not just looking at the negatives—I’m also evaluating the strengths. Do you understand the market? Do you care about what you’re building? Are you going to work hard and learn quickly? Founder quality is absolutely key."

"Doing a startup is an Olympic sport. It’s not a university sport, not an academic bell curve course, and definitely not a pass-fail system. One person gets a gold medal, one gets silver, one gets bronze—and the rest of the world walks away with nothing in that event. So, do you have the right market fit? Can you fundraise? Do you have charisma, presentation skills, and that X factor—the thing that makes people look at you and think, ‘There’s something special about this person’? And of course, we talk about a 10x product. Is what you’re building 10x better than the competition or the status quo?"

Jeremy Au talked about how venture capitalists assess startups based on their ability to scale rapidly, led by strong founders with a clear strategy and market fit. However, their decisions are shaped by heuristics, biases, and time constraints. The best founders move fast, refine their pitches, and demonstrate exponential growth potential. He also discussed how VCs evaluate startups, the common pitfalls in fundraising, and why speed and conviction matter.