Raimie Tang: Student Founder, Redefining Dating & Going All In

Raimie is the Co-Founder and CEO of dateideas , a mobile app that provides couples with unique date experiences for their every date. Today, Raimie runs the largest community of couples in Singapore. dateideas is solving the high failure rate of long-term, serious relationships by providing couples with highly exciting, enjoyable and memorable dates throughout their lives.

Raimie graduated with a double degree in Engineering and Business from the National University of Singapore. As an NUS Overseas Colleges Scholar, he spent one year in Silicon Valley working with the brightest minds while taking classes in Stanford University.

Passionate about disruption, Raimie dedicates his life towards solving extremely challenging problems which uniquely sit on the crossroads between deeply-entrenched social problems and technological innovation.

Jeremy Au: (00:30)
Hey, Raimie, good to have you on the show.
 

Raimie Tang: (00:32)
Hey, Jeremy, it’s great to be here.
 

Jeremy Au: (00:33)
I’m really excited because you are a classic student/founder who started out university and it’s always an interesting thing to see how you’re thinking about things at this point of time and I guess we’ll revisit this in ten years and see how you think about this interview in ten years’ time as well. Raimie, can you just introduce yourself to everybody? i really would love to share your story because you know we had a great conversation about Indonesia, startups, and bootstrapping the last time around, and I think this would be a great conversation for everybody to hear and learn from you.
 

Raimie Tang: (00:54)
Yeah, my name’s Raimie, the cofounder and CEO of dateideas. Today we run the largest community of couples in Singapore with over 50,000 subscribers with over 20,000 weekly active users. Six months ago, we launched our mobile app that provides unique date recommendations for their dates and have since sold close to 100,000 dollars worth of date experiences with double digit revenue growth. For me, my lifelong mantra is actually to inspire young entrepreneurs to solve only the world’s most challenging problems that wouldn’t be solved if they didn’t exist. These are the problems that sit on the crossroads between deeply entrenched social issues and newest innovations in technology. I really wanna inspire and motivate new entrepreneurs to solve those problems.
 

Jeremy Au: (01:40)
Awesome. How did this entrepreneurial bug bite you?
 

Raimie Tang: (01:44)
I think similar to other people, there’s always some program or experience that really was the bug and so back in my national service days, even before university, I always wanted to be a chemical engineer, that’s why I took chemical engineering degree in university. I also qualified for this double degree program, so, I took business as my second degree, but back then I didn’t know anything about entrepreneurship and I participated in this program where they invited entrepreneurs down to speak. I always thought that business never really motivated me because it was buying something cheap, selling at a higher price, making some profit out of it, but during the program, I met entrepreneurs who were super down to earth and through the program, we managed to win the first prize for this mini startup competition. We got a 7,000 dollar grant and the next day, they just transferred 7,000 dollars over, trusting that we’re going to use it for the project. That got me thinking this whole ecosystem is built on trust, reducing the barriers to entry to entrepreneurship. That was a small project that we worked on. We exited that about 8 months in because we realized that we weren’t solving a core problem but those 8 months was really the best time of my life because I would spend hours working on that project and I really enjoyed that. I knew when uni started, that I was gonna go full time on to entrepreneurship, hopefully after I graduated.
 

Jeremy Au: (03:20)
That sounds like fun and this NOC program feels like something a lot of people talk about. What was your experience about NOC and your reflection about that process?
 

Raimie Tang: (03:30)
Fortunately, I entered university already knowing I wanted to be an entrepreneur. I started dateideas even before going on NOC. It made the application a lot easier, thankfully. It was a very small project. For those who don’t know NUS overseas colleges, we get sent to different colleges around the world and I was thankful to go to Silicon Valley. So, I spent one year there doing an internship, also taking some part time classes in Stanford. I think, most importantly, the ecosystem there was something that inspired me. Coming from the perspective of someone who wanted to be an entrepreneur, I was really hungry, trying to gain as much as possible from the whole ecosystem. Every weekend, there would be hackathons. I was thankful I took part in 27 hackathons, every weekend, in the valley and I was fortunate to win prizes for 20 of them but the most important thing was every hackathon I went to, I didn’t go with the same team. I always went alone and wanted to meet new people, form a new team and work on a new idea. That was amazing because at the end of the year, I managed to network with at least 100 – 150 developers or software engineers whom I still keep in touch with today. Beyond that, the valley itself had so many people who were so courageous. I don’t think they were a lot smarter or more hardworking than us, but what they have a lot of is the courage to throw everything behind believing that they’re going to make something work out. When I got back from the valley, much to the disdain of my parents, I decided to take a gap semester to work on dateidea full time because I knew that I didn’t want to come back and become the same person I was before embarking on the journey and I wanted to borrow that guts I felt over there. It was amazing because during that semester, we grew our community from 2,000 to 20,000 subscribers. We managed to get our first 10,000 dollars in revenues. I think that was more than enough to convince my parents and myself that I’m going to do it full time after graduating.
 

Jeremy Au: (05:30)
How did you come up with the idea, were you single back then, how did it come together?
 

Raimie Tang: (05:37)
I think when university started, I was already looking for problems to solve. Of course, best if it’s a personal problem and if not, it’s the people around you have the problem. So easy to get information and insights on them. Yeah, so back then I was also going on dates with one person, but most importantly always a headache and always depended on the males in a heterogeneous relationship to really decide what to do on dates and also my friends were also facing the same problem because they always turn to Groupon back then those Groupon is all very messy. The user experience was really bad and that really sparked the problem to be solved and also a problem that I myself knew I could solve. And yeah so then the next step would be all that happened in layers after that. You don’t want to build a full app from day one. So we started off from Telegram and back then very few people use Telegram back in 2018. In fact I didn’t use Telegram before starting the idea. So I saw my friend was using it. I downloaded telegram for the first time and the first thing I did was to create this telegram channel because I wanted to validate or build an MVP without actually spending too much time and resources, yeah, so I started that. We started getting a 10 or 15 websites to source for potential date ideas to at least provide the supply of content in that telegram community. And yeah after getting their whole pipeline set up, then the next layer would be finding your first users. I think a lot of people struggle with the first 1000 users. What I did was I just send a message to 200 my friends ask them to join this community and I told myself if this community started dropping below 50. I knew that I’m going to just call it quits because nobody saw value in what we were trying to do. But thankfully everyday we grew by a little 205, 210 without me doing anything. I was just doing the content publishing and that showed that people are spreading the word. So I would say it’s important to know from day one that you’re adding value. If if you are doing something that is evident, people leaving don’t get so…don’t believe in your idea so much. You have to be honest and just cut it short and move on to something else. But we are lucky to see traction from day one.
 

Jeremy Au: (07:42)
What’s so interesting about this idea? Can’t people just Google and figure out ideas? What’s so special about this approach?
 

Raimie Tang: (07:51)
I think in the beginning what we know is 90% of couples actually go to Google to look for new experiences. 10% of them go to those typical marketplace apps. Clearly those aren’t very good at solving the problem. But the problem with Google is over 85% of couples who go to Google actually are unhappy with the experience because they spend 45 minutes, one hour to search for something, but all they provide is very generic ideas like go for picnic or go to Marina Barrage and fly a kite together. But it’s not actionable, right? You still need to do so much planning, and that’s where we saw a gap. The marketplace platforms didn’t really serve the needs for couples and couples who went to Google search was still not very happy with the experience. What we wanted to do was to merge both of them. We launched a platform really providing only couple centric experiences. It's a lot more efficient to find what you need to find for a date. But on top of that, we also launched our recommendations algorithm. We realized that there’s a strong correlation between love language of couples and the kind of experiences they kind of enjoy. For example, couples whose love language is quality time, they tend to prefer intimate dining settings or workshops as activities or experiences and couples whose love language is words of affirmation or gifts, they tend to prefer customized gifts or experiences that came with a memento that that they could bring home. So we use that data to really match the right recommendations to the right couples, and we are only in version one of that algorithm and we already doubled our conversion rates. So very excited about that really going deep into this niche and we believe this niche is actually quite big. Yeah, so that’s just the tip of the iceberg but there are other differentiation factors that we have planned out moving forward.
 

Jeremy Au: (09:31)
Doesn’t it feel a bit contrarian. How would you differentiate between the apps that are helping you get a date and what you are talking about which is nurturing and sustaining the relationship?
 

Raimie Tang: (09:45)
The different categories are in the same ecosystem, to be honest, I like to call it relationships ecosystem. A lot of people think that all after dating, the rest can be done on his own, but we don’t think so. I think only today dating apps are becoming more mainstream. Although they launched eight years ago and only today because of COVID, probably a lot more people are very open to chatting I met this person on Tinder, on bumble, on coffee meets bagel, and we believe the second order effect to that is that there’s going to be a huge influx of new couples who've met online who need activities and experiences to get to know each other better over time. The old way of people meeting offline, getting know each other cannot work the same way with people who met virtually, and that’s where we see a more consolidation of this whole ecosystem where the next three years, this dating apps are still going to compete with each other to capture market share because dating apps are going to be more and more mainstream, but then soon enough they will realize that OK, how can they forward integrate their offering to keep the lifetime value of the singles that they match. Our shot is really to grow extremely quickly in the next three years before they start looking at this market and then we are big enough to be plugged into that ecosystem. So after the match is made, immediately, you can have like at least hundreds of ideas for those matches to go to. So for us it’s zero customer acquisition cost. We might even do a revenue share with them at the end of the day, we see them as a potential partner or even a potential acquirer, as the relationships ecosystem becomes more mature.
 

Jeremy Au: (11:18)
It feels like the objective is different. Get a date is not necessarily get the partner.
 

Raimie Tang: (11:26)
Right. The first group of dating apps like Tinder. They focus on casual dating because back then the main market was people who just want the dates and wanted to get that short term thrill of it. But if you look at the latest dating apps and even the recent IPO of Bumble, Coffee Meets Bagel as well, they realize that there’s also a big market of those who are in the dating apps ecosystem to get an actual life partner. So I would say the dating apps which are not so sort of like similar in terms of vision as us is Tinder, but the almost all of the others, like Bumble and Coffee Meets Bagel, they really want to ensure that every match that comes in their ecosystem, they actually lead to a marriage, hopefully. So if you look at their websites they always advocate. Oh, we successfully resulted in like 5000 marriages or 10,000 marriages and I think that’s where the one more of those serious daters to come in. It’s very much aligned.
 

Jeremy Au: (12:24)
There’s a weird dynamic for these dating apps - the more successful they are, the worst economics are for them. If they really help people find a lasting relationship, then the user quits. They want you to have fun, having that happy ending causes them to have that unhappy ending for the app. What’s interesting about you is you’re kind of taking on all the downstream activity, how are you monetizing it?
 

Raimie Tang: (13:34)
Today our revenue model is a commission based approach. Merchants are the ones who pay us 15-20% commissions for each experience that’s booked through our platform, but moving forward we are also experimenting with a subscription model because we realized that our retention rates are really high. Every month, at least 50% of our users are repeat users coming back to look for new experiences to purchase. So we actually exploring a subscription model where either we only show exclusive date ideas that cannot be found elsewhere and pay a monthly fee to get access to that or they just buy for the next five months five different dates and we promise at a cheaper price but also they at least they come back to our platform to book all their dates. That’s I mean going back to the point you brought up too. Everyone knows that the unit economics for dating apps is very contradictory. After they match, they leave the platform. They don’t want them to leave and want to come back again. They want those people to come back again so they can extract more lifetime value from their customer. But that’s why we believe because our downstream activities basically throughout the rest of the relationship. So there’s a very good way for these dating apps to extend that lifetime value through a partner, rather than them having to launch that one feature.
 

Jeremy Au: (14:43)
That will be a really interesting dynamic because for them, if they’re smart enough to expand it themselves because they already brought a relationship together, they’ve acquired the brand and the customers. It’s only a matter of time until they do so. A Tinder subscription, 5, 10, 20 bucks. If I like you as a date, I’m going to spend 100 dollars on the meal and then on the third date, I’m trying to impress, we buy flowers, we buy gifts. There’s so much more transactional value happening downstream of it. How do you see yourself building that out over time?
 

Raimie Tang: (15:22)
Basically our vision is really to empower couples relationships. Eventually we don’t see our date ideas marketplace as the only feature on the app. We see that more of a subset of the entire ecosystem offerings where we want to provide tools to help couples understand each other better emotionally. So basically helping them take quizzes every month to at least keep them up to date towards what their goals are, whether they’re changing in terms of personalities, or whether they need to realign each other. And I think that’s where the more of a subscription model come in. When we launched these other tools where the marketplace is free, they can buy and pay the commission every time a transaction is made. But the other subscription features will be a premium feature for them too, if they’re really serious about making sure their relationship is maintained and sustain for the long term. Of course, counselling and therapy might be one of the features that we launch, also helping couples align financial goals better because that’s one of the top things that couples quarrel, argue, breakup, and all these come and show themselves in our quizzes to make sure they're aligned
 

Jeremy Au: (16:27)
How have you used your own service for your own relationship,
 

Raimie Tang: (16:32)
I think it's very effective. Basically, 'cause I think for me our target audience is really busy young adults who don't have that much time to plan everything, all all basically don't have time to go to Google search, spend one hour to look for something. So for me is super easy, right? I just filter the date which I’m available because I’m not the most free of people and then immediately I get a very curated list of those activities that are available. And then of course I can filter by location again. Then I get this. So every week, right? Our team actually updates new ideas and I don’t directly manage that, so I’m even impressed, right? Like recently there’s a cotton candy bouquet workshop which I couldn’t. I didn’t understand that such a thing would exist, yeah, but I just booked that recently. So yeah, so many things that I can go back for very thankful for, like our own platform.
 

Jeremy Au: (17:23)
And your partner is also very happy for it as well.
 

Raimie Tang: (17:25)
Yeah, I mean, yeah. And so in fact, funny enough. What we realized from our data is again, in a heterogeneous relationship the women are the ones who browse a lot more, but the men are the ones who book and make the purchase. So we are actually launching this couples linking feature where we allow the women to just bookmark things that like. And then it’s very efficient for the for the guys who like, oh, OK, the the person like this. So my goal is really as the male in the relationship is to make my partner happy. So yeah, I think very exciting when we launch that feature.
 

Jeremy Au: (17:58)
I can imagine that will help a lot of debates. In any relationship, it’s hard to be telepathic. Could you share with us one of the dates you used your own platform for your own relationship, how did it go?
 

Raimie Tang: (18:18)
Yeah so funny enough we have this experience on the app itself where you is called special occasion planner. Someone on our team will jump on a 15 minute call after the person purchases this planner and then he or she would talk to the customer about what does your partner like? You want balloons and all that, ‘cause it’s meaningful special occasion and then after that conversation so we charged at about $50 Singapore dollars for that. Of course, the additional bundles that come along side is of course have to be paid by the customer itself as top up. So just really planning service so very thankful for birthday celebration I mentioned. I mean I wouldn’t go so much the details of what I got, but yeah. Very thankful because everything was delivered by our team itself, so they got a very big balloon and flowers and I didn’t have to do anything. All I needed was to show up and then everything would be fulfilled for me. So yeah, it was a recent birthday celebration and very good ‘cause we ended up going to the rooftop at Marina Bay Sands. Have a meal and then after that there was a surprise and. I didn’t really have to call my friends. Hey, can you prepare this surprise for me is all our own team handling and fulfilling that so very yeah. I think that so far that special occasion planner has sold quite a lot so far although we launched it about just a couple of months back on the platform.
 

Jeremy Au: (19:34)
What does the future look like for you from your perspective?
 

Raimie Tang: (19:38)
Yeah. So, of course we don’t see ourselves as just a Singapore player. I think as a young entrepreneur a lot of people think that all in some of the bigger companies who made the mistake where they stayed too long within Singapore. And we definitely don’t want to do that. Of course, now it’s a bit hard because of COVID, but the upcoming features that we’re launching we are planning to be scalable across borders. So basically we want to generate sort of build a community of couples. It’s not just tied to Singapore and having date ideas as a marketplace alone is very hyper local. It’s not going to workout, so I mentioned about a quiz I mentioned about having forum on the on the platform where couples can launch their own quizzes for other couples to take and evaluate their own relationships. Being able to upvote, downvote. It’s really that kind of community that we are building and that’s what we’re excited about. Because then couples in other cities can compare their own relationship dynamics with other couples of in let’s say Singapore first, and that’s where we really create an ecosystem. So today we actually started building a community of couples in the Philippines on TikTok. Although we started about a month back with over 6000 couples in the community already. And that's really what we're excited about. Really scaling fast across Southeast Asia and seeing how we can replicate certain features that have succeeded in Singapore to those cities and how we can use that as a network effect creator over time. Yeah, so going out Singapore. Of course, a lot of inexperienced entrepreneurs might be scared, but to me I think it's very exciting. It's a whole new world, bigger market as well.
 

Jeremy Au: (21:03)
As you do all of this, I’m sure you’re learning a lot because you’re younger than me, right? Just out of college and that reminds me of when I was out of college building my first company as well and I remember it was a very tough…exciting moments, but also tough times. Could you share about any tough times you had and how you had to be brave?
 

Raimie Tang: (21:23)
I’m so thankful you asked for this because so far it seems like all is good and all’s exciting, but the truth is, there’s so many tough moments. One hour alone is not enough to list all of them, but I would say one of the toughest moments is of course finding a strong enough cofounder. I self-learned coding, but I knew that my strengths lie in really being a CEO rather than CTO. So I was really looking for a cofounder for the longest time. Message over 300 people on LinkedIn or cofounders lab and a few other co-founder matching platforms. I met up with over 50 of them in person and over zoom and even tried working with two of them on probation period but none of them really fit the bill. So I was really on my wits’ end and I was so prepared to really become a solo founder until I managed to chance upon Arvind, our current CTO and that took me like one and a half years to finally find him, but the difference is when I first started working with him he was really like a match made in heaven for lack of a better term. I mean, since we are also in the dating and relationship space, yeah, so it was so amazing where suddenly, the other two guys before him. It really was so obvious at the moment that they weren’t the right fit and Arvind and myself, we align super quickly and we complement each other’s strengths. So I would say that would be one of the biggest challenges. And of course others as well. Right now we’re fund raising very thankful because we managed to close more than half the round already and then we started not too long ago, but of course the. In the early days as well, it was hard to convince investors. But yeah, that’s also another challenge. As you climb every mountain, I realized that you would think that, oh, this is the toughest mountain I've climbed. But then again, you, you meet with an even higher mountain and then the previous challenge didn't seem so hard anymore. So that's when you know you're really growing and I'm glad so far we are meeting even tougher challenges and slowly but surely we are overcoming them one by one.
 

Jeremy Au: (23:10)
The cofounder is an issue for lots of people. It’s even more painful especially for people who are younger in their careers because if you’re fifty years old, you’ve probably worked with thousands of people, so you already know who’s the good one, who’s the bad one. If you’re new to the career or to the vertical or geography, then those things become much harder, you’re starting from scratch. You were using cofounding matching platforms, having conversations, doing calls, what was your process like?
 

Raimie Tang: (23:46)
I’m very thankful because I have both business and engineering background so I like to make things very structured at the start. Of course, what I did was I went to LinkedIn I was thankful because there was a one month free premium trial, right? So I had unlimited search and all I did was I really searched adjacent platforms in the market space where other software engineers have spent like 3-5 years in so I reached out to them. I also went to find NUS Masters students ‘cause I really want that really strong technical cofounders rather than just one of my peers in my level of university. I think they lack a lot of experience. So yeah, I started off going to LinkedIn and then going to the NUS website like stalking them on LinkedIn, seeing what they’ve done and reaching out the relevant ones, and then made about 150 of the early people I reached out to. Then I went to cofounder matching platforms like CoFoundersLab, so that’s a bit different because they already have a curated list of people who are interested in entrepreneurship, interested to start up. So I ended up going more to those and going so some of the problems don’t let you see the LinkedIn profile. They hide it unless you pay the premium subscription, so I was very thankful for this platform CoFoundersLab. They allowed me to find a LinkedIn profile for those and yeah, they got me another 50 to 100 leads after narrowing down. I think more importantly there are tools out there and, of course, a lot of it might be scrappy. I strongly suggest not settling for just the people who are within your network because I went through that as well. It didn’t read the not the best for me. After really expanding my network and having the confidence to really talk to people who seemed a lot more experienced. I think it really made me grow faster as well.
 

Jeremy Au: (25:25)
That’s something you’ve been able to build out over the past few years. You mentioned that you had a couple of candidates and your cofounder was clearly better. Let’s walk back. What was that like, you were working with them and feeling it’s okay, but not great, what was that feeling like?
 

Raimie Tang: (25:57)
It’s like product market fit. I think I always thought maybe I have to compromise. Maybe this person is lacking in something as small as being punctual for meeting. I just need to educate him or her. This is what the culture should be like. And then there’s other things that he or she would be good at. But yeah, there’s always a balance or compromise we had to align. Maybe something they weren’t happy with what I said and then we have to jump on a separate call to just align that and say OK, this how we function the reason behind it. And so I thought there was a norm and I believe many inexperienced founders would also think, yeah, it’s normal. It’s just our founding team we are going to go all the way. Although there are some friction between us. But that’s always bad because it only gets worse over time. Back then I convinced myself that it was OK. I was very thankful because after 2-3 months I managed to get some mentor who told me that hey, you should really cut it off early. So I told them they didn’t clear the probation period and that’s where I met Arvind. I think the core difference again, like product market fit, it doesn’t feel like a pull anymore. It feels like a push. Even from day one, after I met Arvind for the first time, I felt like OK, maybe not at this time I should just be a solo founder. But even after that he kept messaging me here I have some new ideas that I feel like can be amazing for the platform. I have some code I’ve written that can be replicated and you don’t need to write new code and all that so it felt more like push, him wanting to be part of the journey as much as me wanting it to work as well, so I think that was a very big indicator which I wouldn’t have thought would be a good indicator and after. I wasn’t really keen on bring him on board so early, but he just kept pushing and I was OK. Let’s just give it a shot. Immediately after that, we jump on 30 minute calls every week, catch ups just to make sure we are aligned. It’s really like it’s super aligned, so I would say thereafter, the signs a lot more obvious rather than or if you even if you need an extra call to align certain miscommunication, I think that’s a bad sign you need to track that properly to see whether these miscommunications happen often, if it happens rarely, then I would say it’s good. On top of that also, expectations of each other need to be equally high and also equal. If, let’s say you thought that he’s going to put in effort in this feature and or this part of the product, and then the output is not as high as you wish. I think that’s a very bad sign also. Even if you do soft convince him this time around here, you need do it better the next time round is still off the charge. I think that’s a very big red flag that you should immediately reconsider finding a new co-founder.
 

Jeremy Au: (28:25)
That’s an interesting dynamic. If it’s not perfect, is it because this is not the right fit or something we can work through. That’s a tough moment for everybody to be thinking about. What advice do you have for people who are trying to make a decision? There are so many founders walking around with sub-optimal pairings. Sometimes it’s them. Sometimes, it’s the other person. Sometimes it’s the fit. How do you give that advice or think about it?
 

Raimie Tang: (28:56)
This is a very tough answer. Of course I would say in my opinion, because of past data points with other founders, there other teams which really went to Series A Series B and then split up, there are teams that managed to really cut the butt early before anything bad happened. Yeah, but I would say those who are meant to be good entrepreneurs will stay. No matter what. What that means is if we are good and it’s not your fault but your cofounder’s fault somewhere along the journey that personal leave or y’all was split and then you move on to something greater than that. At times, if the whole team is bad, then either way whether you use stick or you split it wouldn’t work out that well. I would say the most important thing is it’s more of a natural selection over time. If you really believe. If an entrepreneur really believes he or she is the one to succeed, then I advise that person. If you sense any red flags early, just cut it off and move on with someone else. You might have to give up some shares because some vesting period, it might not be the most amicable of like conversations, or you might be scared of their conversation, but I feel if you generally believe that you’re going to succeed one day, it’s better to cut it off earlier than later but for those entrepreneurs who don't have the guts to cut it off and admit that they don't have a strong team, I highly doubt that they are meant to do entrepreneurship in the first place. To be honest, because it's very logical that the earlier you sense problems, the earlier you should really solve them rather than waiting and postponing that to another date which will come back and bite them even harder, yeah, I hope that clarifies. For me, I think I also applied, every founder would think, yeah, I meant to do entrepreneurship. But the more data points and the more you doubt your team yourself, then the more likely you think that OK, this is not for me. So yeah, I think like the earlier you sort these out, the better.
 

Jeremy Au: (30:38)
In walks in Arvind and it felt good because he kept pushing you and being enthusiastic and everything. You were already thinking of being a solo founder because you were so frustrated. You had gone through a thousand names at this point? So, what restarted your faith in not being single anymore and being a bachelor?
 

Raimie Tang: (31:03)
Thanks for the analogy, it’s very apt. I would say again, I was still suspicious right? Although it felt like he was interested, I commenced working with him. I was still very cautious ‘cause I didn’t want to really like sign something official so early. So actually told me one year of working with Arvind to make sure that we signed a proper shareholders agreement/founders agreement. I think one year is a good threshold to have a probation period. In my opinion, of course, the longer the better, but I think one year is a good time. If six months you probably have to work a lot before you sign anything, but I think one year is a good time. That was good because Arvind, he wasn’t so pushy. I think he was also logical, mature enough to know that, hey, there’s no point signing agreements until we know that we are good fit because if not, we’re going to fail anyways, so I think that was a very good sign and only when it's time to really open that we both agreed it was the right time and we both agreed that, hey, we’re going to do something amazing together. But if that conversation came up and like someone one of the founders would think like actually I’m enjoying my full time job. Can do this on the side and then the other founder is like I'm going to do it full time, then I think it's never a good sign because you’re not putting the similar skin in the game. It’s just going to break up eventually.
 

Jeremy Au: (32:15)
Doesn’t it feel scary for someone like him to be putting in a year of part-time/helping out work. Feels kind of stupid, no? If you were his friend telling him hey you’re giving out a year of free work. How did you think about that?
 

Raimie Tang: (32:30)
To provide some context, he’s a software engineer at Grab and he worked in Bloomberg in the past also. So he’s giving up a lot and I think the biggest thing that converted him was probably knowing about my capabilities and understanding how passionate and serious I am about building a Unicorn one day. I think that’s what really convinced him ‘cause even ideas that could be the most amazing idea, but at the end of the day, it’s the people who find the pivots and tweak the business model to succeed. So if I want to point to one thing that really convinced him, if you would want to call it, there’s a more for questionable decision of putting hours in for one year, I would say because every meeting we had every conversation we had and every sort of like small project we worked on together. It was a good sign for him that like I think, the way I behaved the sort the output I provided convince him further. Hey we might be onto something big, yeah, so I recommend a lot inexperienced founders or people who are new to entrepreneurship. They think that as long as I do a good job, things like culture doesn’t matter. The way I behave around people, it doesn’t matter that much as long as I do so much better in the work that I do. But it’s a very flawed idea. It's a fallacy because. Every single small behavior or action is actually a data point for investors for potential partners for potential cofounders to see whether you are really going to succeed or not. I was lucky to learn that very early. I mentioned to tweak their team culture to be one that’s very high performing and because of that, I think Arvind was convinced that I had ability to really align different individuals together to achieve something amazing.
 

Jeremy Au: (34:07)
As you do all of this, you were doing all of this while in college. Other people are off doing CCAs and extracurriculars, dating around. You get to date and do the idea at the same time. What’s interesting is that you graduated a few months ago, right? Now you’re seeing all your friends become bankers, consultants, join a tech startup, be a PM, were you ever tempted to just join a normal career?
 

Raimie Tang: (34:39)
The answer is no. I think this is a very fundamental question. Of course there are different people of different backgrounds. I’m fortunate enough to be able to do it full time without worrying for at least the next three to four years about finances, so I don’t think it’s suitable for everyone because some people really have to earn to really feed the family and all that but I would say if there was even a thought in your mind that I have a backup plan, then it’s actually artificial ceiling to how far you can go in entrepreneurship. You keep thinking, OK, I don’t even put in so much effort because anyway that’s a job in McKinsey waiting for me. Or I can just go into investment banking career and then it becomes a self fulfilling prophecy. That actually happens eventually. From what I know, the best entrepreneurs, especially those that came out from college are those that don’t even consider that as an option. It’s either all in or all or nothing for them. And I think that’s the same for me. Similar as me, they started from college, they seem very serious and they manage to get even better traction than I did. But when suddenly a carrot came dangling and then they jump over. It’s not a bad choice, but I think they actively make that decision. I would say they probably aren’t ready for entrepreneurship yet. Not saying they won’t be in the future. But yeah, I think I always doubt people who always have this backup plan in the back of their mind.
 

Jeremy Au: (35:54)
At this stage you’re out closing the round. There’s still an 80% chance of failure after closing this round, right
 

Raimie Tang: (36:01)
90%, in fact.
 

Jeremy Au: (36:02)
90%! Well, I think you’re better than the average, so, let’s just say 80%. How do you feel about those odds now?
 

Raimie Tang: (36:10)
I think at the end of the day there’s two principles I feel are important being a young founder and 80% failure rate. Number one. Manage cash flow no matter what, as long as you have revenues as your costs. You see the amount in your bank and so you keep your costs below your revenues or even if you burn you know you have that much runway. I think no matter what, the longer you stay in the game, the higher chance of success. Of course there are some people who are able to burn faster because of different resources provided to them, and of course with more resources to higher chances of success if you do it the right way. But I think cash flows important for people like me who doesn’t come from a very rich background and doing for the first time. I think one thing to add with this point, if you compare young founders with older founders who have a lot more experience, a lot more resources, a lot more network than you it might seem like all young founders are totally disadvantaged, right? There's nowhere right if I invested company, put your money in the more experienced person in the younger person, but I think what we have a lot of is time, and this is something that the older folks can never get back and you look at people like Elon Musk. Why is he starting SpaceX test line and a bunch of stuff is he’s not competing with the competitors in the space, but rather he’s competing with time because he wants to achieve all this as soon as possible and and live to see the day it succeeds. Yeah, So what young founders have is that time and hence in my opinion, the longer you stay in the game and you don’t die, the higher your chances of success and because you have that 20 odd years to play around with and that’s a huge advantage. So that’s the first thing I think the second thing as well as being open minded and adaptable if you have time but you’re so close minded and just doing the same things over and over again despite what investors tell you, despite what your users are telling you. For example, even for me, if this dateideas marketplace seems like hey, we’re not hitting the adventure back growth that we’re looking for. I think being super open minded to search for pivots is crucial. I don’t subscribe to the view of believing in your vision and really like putting that much hours despite the signs showing ‘cause maybe being an engineer, I look at data points and it's a lot more important because there's two different thoughts, right? Schools of thought, right? One is to stay true to what you believe in, and you'll succeed eventually and then the other school of thought is you need to be smart and go where the market tells you if the signs are not showing then so in my opinion the former works, but it's highly dependent luck only if the market changes. If let's say you're not going down the right path. From the get go and only if the market changes in a very fortunate way. Suddenly like what you're working on, suddenly catches on, then you might succeed, but if you’re of the latter school of thought where you are very aware and alert on what the market needs and then slowly tweaking yourself towards that direction, then time as an advantage is super valuable to help you get there eventually. Yeah, I think these two things are super crucial to of course optimize. Now it’s 80%. Slowly slowly as you spend more time, as you become more open minded and more aware of things. Slowly, that percentage of failure will deplete over time.
 

Jeremy Au: (39:06)
Amazing, Raimie. I just want to use this time to paraphrase the three big themes that I got from this conversation. The first of course is thank you so much for sharing the reality of being a student founder and now out there to go there full time. And I think those as a really interesting point of view just to walk through that chronologically. But also from a personal perspective, why does it like to kind of like go through that whole ideations to founder match to building, and so on and so forth, so I think it’s is a fun set of experiences. The second thing was thank you for kind of like having that conversation about dating versus relationship apps, but also going into a little bit more about the economics and transactions versus the value and solutions/value proposition and benefits for different people in the market. And I think that’s a really interesting dynamic because I don’t think most people are thinking about it beyond just being consumer of the app versus actually someone being on the other side of it. The third thing I think that’s interesting that you talked about is talking about risk. And talking about whether you have done it or not done it or anything whatsoever. So I think that's a really interesting dynamic that you had. Thank you so much for coming on the show.
 

Raimie Tang: (40:18)
Yeah, very happy to be here. Thanks so much for inviting me