# S01E01 · Transcript — Eric McHugh Full transcript of [The Useful Podcast](https://useful.ventures/podcast) Episode 1, a founder-to-founder conversation between host Gokul Bala and Eric McHugh, President of [Dataing](https://dataing.io) and co-founder of the AI dating app Cupid. Back to the [episode page](https://useful.ventures/podcast/eric-mchugh-dataing). This transcript has been lightly edited for readability. Filler words and false starts have been removed and the meaning has been preserved. Any errors are mine, not Eric's. ## Before Dataing **Gokul** Nice to meet you, Eric. Welcome to the show. Before we get into it, this is your story, told your way, so you're in full control of it. If there's anything you say that you don't want out there, tell me afterwards and I can cut it. I'm curious about your journey before Dataing. I guess you pronounce it "dating," right? Before that there was Aces Fund, and before that you had Cart Rev. What made you a builder? How did you get into the space? **Eric** I graduated from UC Irvine and did the typical after-college thing — lawyer, doctor, consultant seemed like the path. I joined a consultancy firm helping Fortune 500 companies go through bankruptcy. At the same time, I was getting really into cryptocurrency. The cool thing about consultancy is if you bill out hours, you're generally good, so I could do my work while listening to podcasts nonstop. But the ethos of the firm didn't align with the ethos behind Bitcoin. In the bankruptcy process, creditors get paid off in four tiers. Group one first, group two second, and so on. The mom and pops, the everyday person, they always end up in the last bucket. I didn't like that. So I waited till I got my bonus, quit without a plan, and started going to crypto meetups. I met the original Aces Fund team in 2017 — it was called Split back then, incubated in Santa Monica. We were whiteboarding late one night and that idea spun off into Cart Rev, which ended up VC-funded and incubated at Science Inc., one of the best incubators in California. Cart Rev was TikTok Shops before TikTok Shops existed — a way for Shopify brands to upload products, and for influencers or everyday people to multi-checkout from different brands in one go. The brand gets a sale, the person gets a commission, the customer gets a discount. Win-win-win. Being young at Science Inc. was huge. The incubator was structured like floors — ground floor startups, and the better you do, the higher up you move. So at an early age I was surrounded by founders at every level, in every vertical. That gave me a massive boost in career trajectory. We launched ShopX, which did well at launch but eventually died out. While promoting it I did a podcast tour — I genuinely love podcasting, you meet cool people. I stayed in touch with one host, Mark, who ran a podcast called *It's Crypto Economy*. We'd send each other stuff on Instagram. Then this AI dating avatar started following me on Twitter. It looked like Cortana from Halo. Turns out it was Mark. He said he was thinking about building an AI dating app. I thought it was funny, thought it could help a lot of people, and here we are. **Gokul** There's a lot of different things in there. Even before that you did dark matter research at Carnegie Mellon. What's the thing connecting all of them? Or is it just flowing into everything? **Eric** I follow whatever excites me most at the moment. It looks random, but I look at life like chess. You may have made the best move or the worst move, but the question is always: what's the best move from here? I also believe in a creator, and I think excitement is a signal that you're on the right path. **Gokul** I love the game analogy. I think of life like a card game — you just play your hand as best you can. One thing I've heard you say on other podcasts is that you're always the least qualified person on the team. From the outside I don't think that's true. Do you actually believe it, or is it the hunger to do more? **Eric** I view it through the lens of authenticity. I'm the number one me in the world. If I do what I'm authentically good at, I'm number one. But you can't beat me at being me, and I can't beat you at being you. So when you build a team, you let people be their authentic selves and do what excites them most. If they're in their flow state doing what they do best, of course you're underqualified compared to them. That's why they're there. It's a win for everyone. **Gokul** That's the Doc Rivers quote — champion in your role. Are you a Boston fan? **Eric** I like your fan, but Doc Rivers is a great coach. Underrated. You have to respect coaches like Doc and Pop. I'd never say anything bad about either of them. **Gokul** I'm a Golden State guy, and recently a Spurs fan. **Eric** Wemby is going to be great. He just looks like he's going to win. ## Building Cupid **Gokul** Going back to Dataing — you were chief growth officer for three years, and now you're co-founder and president. What's the role shift? **Eric** Honestly there isn't much of a shift, titles only. Titles don't really matter to me; they're more outward-facing so people trust the brand when I go on podcasts. My job is pretty much the same. It's an early-stage startup, so you do a bit of everything. My main role is user acquisition and retention, and that loops back into tech — users tell you what they like, what doesn't work, and you feed that to the dev team. I'm the glue guy. I stick my head in a bunch of departments but mainly lead marketing. There are three founders: Mark is CEO, Leo is CTO on the tech side, and I'm on growth, business development, and partnerships. **Gokul** Are you operating mainly in the US? I tried to get the app in Canada and couldn't. **Eric** We had V1 live in the US App Store for a while — that's why you couldn't download it. We used it as a learning experience and built V2 based on all the feedback. V2 launches in a couple weeks on iOS. We also have a global web app, so you can use that now. **Gokul** I saw a comment on your LinkedIn that I love: if a dating app makes a happy couple, those two people leave, so they lose the paying customer. Every app is incentivized to keep people single. What does Dataing do differently? **Eric** The three big issues with old-school dating apps. I use Match.com as the example because they own most of them — Tinder, Hinge, the market. First, it's basically "hot or not." Is this person good-looking, yes or no. That's a terrible way to get a match. Second, the top ten percent of guys get access to everyone, which creates a skewed marketplace. A "10" guy matches with a "5" girl, the "5" girl now thinks she's a 10 and ignores the "5" guy. Only the top feast; everyone else is unhappy. But the biggest issue is the incentive structure. Every time Tinder or Hinge matches a happy couple, that couple leaves. That's a lost paying customer. So they rely on churn marketing — keeping people on the ferris wheel. Delete the app, download the app, delete the app. That's all by design. What Dataing does differently is support before and after the match. We auto-generate dating profiles based on your digital footprint. You connect sources and photos, and on the back end we generate tags based on your personality — 0.8 correlation with skiing, 0.7 with pizza, 0.9 with being close to your family. That generates your profile and your matches. If you're into skiing, you might match with someone who has a high correlation with snowboarding. Let's say you match with Ashley. You see an AI-generated profile of her — AI-generated so people can't lie and make it up. Since we have that profile, you can ask Cupid: "I'm into skiing, she's into snowboarding, what should we do for our first date?" Cupid gives an answer based on both of your contexts, not just yours. This solves the AI psychosis problem — people getting jazzed up by AI and asking it things it wasn't meant for. Cupid takes both people's context. And it's always learning. If you say, "No thanks, I don't like that for these reasons," it updates your profile. You start doing pickleball, it adjusts. You stop, it adjusts. And it's more powerful than planning a date — you can ask "What are three red-flag conversation topics we should avoid?" or "How do we best work together?" We're incentivized to generate the match because we support after. **Gokul** Do you monetize the data? **Eric** We're not monetizing yet — we're bootstrapped. The plan is twofold. First, a system where Cupid suggests and books a date within the app, and we take a commission. So we're incentivized to make a good match — if people like our dates and book through us, we get paid. Second, opt-in ads and offers. If you want to receive ads, we get paid and share the money with you. If you don't, also great. ## Refusing to vibe code **Gokul** I've read that you refuse to vibe code. I'm curious about your angle on vibe coding and AI tools. **Eric** I'm not totally against it. Vibe coding can create apps and do a bunch of stuff, but it doesn't scale. The biggest issue is that if you keep prompting an LLM — Claude, Codex, whatever — it accumulates technical debt really quickly and leaves holes in the security system. That's very difficult to scale. When I say we don't vibe code, I mean our app is made by actual engineers with senior-level experience who are leaders in their field, leveraging AI. We're not a vibe-coded app. We're an app made by engineers who have a much better understanding than the normal vibe coder. Vibe coding is cool for prototypes — we've vibe-coded a bunch of features to test them out and it actually kind of works. But for a global system, it's not the way. **Gokul** I thought you guys weren't using AI at all. But you're AI-native. **Eric** Our dev team is incredibly AI-native. They crush with AI. I'd say I'm anti-AI-slop, not anti-AI. **Gokul** It's the thoughtless AI — soulless. When someone recursively uses AI to generate the idea and execute the idea, it's just slop on slop on slop. **Eric** Yeah. People can pick that up, and I really don't think people like it. So it's leaning itself out, which is nice. ## Ten days of silence **Gokul** You did a ten-day silent Vipassana retreat. What was your mindset going in, and why did you do it? **Eric** It's been one of the most transformative experiences of my life, and one of the hardest. What got me into it goes back to the incubator stage. I was around people older and smarter than me, and I noticed all the most successful ones had a spiritual practice. I was go-go-go — first one there, last one out, always moving forward. One mentor I talked with a lot, I asked him to grab lunch on a Tuesday at one. He said, "No, that's my meditation time." I thought, what do you mean meditation? You just sit there? As a kid I ignored it, but it kept coming up. I started trying to implement it, and once you start, the algorithm feeds you the right content. The books, the YouTube videos — it all fed into it. A friend recommended a Vipassana retreat. I signed up without researching it. Up until the day I arrived, I didn't know it was a silent retreat. Ten full days of pure silence. The day you arrive doesn't count, the day you leave doesn't count. You aren't looking at anyone, you aren't talking with anyone. You wake up at four, meditate, have breakfast, meditate, have lunch, meditate, and at the end of the day there's a discourse taught by a teacher who's actually deceased. The logic is this: if I meditate for an hour after this podcast, the moment I'm done I check my phone, go on Twitter, check LinkedIn — the meditation stops. If you don't have that, it continuously goes. It's the method the Buddha used to reach enlightenment. For the first three days you focus on the area around your nostril and pick up sensations. Then you scan your body back and forth, over and over. It pulls out traumas you've stored throughout your life in the form of sensations. Like running metal through magnets to extract impurities — you're doing that on a spiritual level. From a business perspective, it's interesting how the guy scaled it. The man who brought it to the US was a businessman in India, and it saved his life. Each center is standalone and donation-based. I can donate as a student; you can't. All the food and facilities are run by donations, and the workers are past students giving back — they call it Dharma service. Within five minutes of dropping you off, it's so well organized you could serve the current students. He crushed the scalability. **Gokul** What were your first thoughts coming out, coming back to civilization? **Eric** Right after we broke the silence, that was the happiest I've ever seen a group of people. Everyone was just chilling and eating. It was a very diverse group — ex-moguls, war vets working through trauma, older tech guys from Google and Facebook just chilling at fifty, a friend of mine whose job is rock climbing and odd jobs. Nobody cared about job position. They were just happy to have gone through it. The immediate impact: outer reality reflects inner reality. What you send out, you get back. The way you close out the meditation is you focus your energy and wish everyone in the world peace, love, and happiness. I started doing that more consciously, and I noticed real benefits. At the gym, I started mentally wishing people well — "great workout, crushing it" — and people started being more friendly to me. Fist bumps, high fives. I do it before every business call. Before this podcast I wrote down: I'm grateful I get to meet Gokul, he seems like a nice guy, I'm sure it will go well, and if there's anything I can do to help him, let's do that. If I'd gone into this like "I don't really want to do this, it's late," it would drive the direction of the podcast. I do it before every meeting, every interview, every live event. The energy you put out comes back tenfold. From a business perspective it makes sense; from a spiritual perspective it makes sense. **Gokul** I love that mindset. I've read *The Secret* — the Law of Attraction. The mindset you walk in with shapes the world you see. **Eric** You're filtering all your sensory data through your experiences, and you're missing tons of stuff. If you view it through a negative light, you notice the negative. If you view it through a positive light, you notice the positive. Negativity and positivity both expand. A small positive thought leads to the next positive thought, which puts you on a train of positivity, and your decisions come from that place. I like to get myself in the right headspace before I make decisions. ## Why Dataing, and the hardest part **Gokul** What made you want to join the app? Was there a personal experience, or was it just a cool project? **Eric** It's more that it could help a lot of people. I'm thirty-two, I've been on the apps for a while, and I know they don't really work. I've been there. A better alternative should exist. My logic is that it puts people in the best position to succeed. You can match on an app perfectly on paper, but you still have to meet in person and vibe with them. I personally like to meet girls in person — it works best for me. But if online dating is on the rise, might as well give people a better path if they choose it. **Gokul** Over the last three or four years, what was the hardest moment with Dataing? **Eric** I don't even view it as hard, because I'm following what excites me. The hardest part is the fundraising process — and because we're bootstrapped, it's saying no. You see competitors copy what you did, get VC-funded, get that big push where everyone's talking about them. Then you watch them die out, because VC money isn't free — you have to listen to them. We haven't taken VC money. We've outlasted pretty much all the competitors and are doing better than most who took those massive checks. Saying no to money has been the hardest part. We're pre-revenue, burning through credit cards and savings, but it's built the product we love, and it's forced us to be scrappy — we found ways to run our LLMs locally. In the long run it helps. **Gokul** Innovation doesn't happen when you have everything given to you. You have to struggle a bit to actually innovate. **Eric** It's balance. The more in the negatives you are, the more in the positives you will be. ## The version of winning **Gokul** What's the version of winning for Dataing? **Eric** The big grand master plan is a billion happy couples. I view it as a way to leave a positive impact across generations. Even if Dataing matches one couple that wouldn't have met, and they're a great couple, that affects everything — their kids, their family. Scale that to a million couples and it's an impact that lasts generations. Something we're building now is the API. People are building on top of Dataing. We offer personalization and monetization if you know your users. Someone's building a recruiting tool — you can see how a candidate vibes with the team, not just their competency. Someone's building something for raving culture — find your rave crew based on commonality. Another partner is doing in-game matchmaking — who you should team up with from a personal level. It's about driving human connection. A bunch of people building what they want on top of our app — they get the benefits, we get the benefits, the user gets the benefits. Win-win-win. **Gokul** That's how you reach the billion happy couples. **Eric** And it feeds back into Dataing. If someone uses the in-game app and thinks it's cool, they might check out the dating app. They already trust the product, so they trust ours. ## Crypto and agents **Gokul** You've said technology should make people more human. I also believe crypto and agents are the perfect kind of currency for agents. Do you think you'll go back into crypto? What's your take on agents and crypto? **Eric** I follow what excites me most. I got burned out on crypto because of the scams and hacks, but we are working with crypto — we just don't market it to the dating app user. We're building a data marketplace on top of the Stacks Foundation, which is an L2 on Bitcoin. They gave us a grant to build it. Here's how it integrates. You're on Dataing. Do you want ads? Yes or no. If yes, you get paid. At the same time, if you want to sell your data — and agents love data, the better the data the better the agent serves people — you click yes, your data gets listed on the marketplace, and if an agent buys it, you get paid in Stacks. If you don't want to, that's cool too. And if you delete your account, everything is deleted. Nothing is saved. **Gokul** Your data's getting sold without your knowledge anyway. You might as well get paid for it. **Eric** Exactly. Google and Facebook are already selling it. Imagine instead of paying five bucks a month for Hinge, you get paid five bucks a month. You're not paying for an app; you're getting paid. ## The biggest learning and the legacy **Gokul** Over the last couple of companies, what were your biggest learning experiences? **Eric** Early on, learning to work with development teams and map the end-to-end from concept to full product was the most valuable. You have an idea — how do you actually build it? You break it into stories, archive them, move them along the line. But honestly the biggest thing has been the spiritual aspect. I don't think in my nine-to-five I'd have had the attention or met the right people to go down the spiritual path. Having that base has reflected in the products and the people who support them. Dataing is intended to help people. Cupid AI is built on Hermeticism and the Law of One and other spiritual teachings. If it's on that core, people feel it subconsciously when they chat with the AI, and it actually helps them. **Gokul** At the end of your career, what would you want people to remember you for? **Eric** Being kind. **Gokul** Come on. Most founders don't become founders unless they have some fire, some secret goal. What's yours? **Eric** Honestly, I want to erase myself from the internet completely and just chill. I'm going on a bunch of podcasts now, but eventually I want to remove myself and just retire nicely. The positive impact of matching couples is how I leave a mark. I view everything in terms of vibration. David R. Hawkins has a chart where each emotional state has a different vibrational frequency — love, peace, joy, and enlightenment are very high; shame, fear, and guilt are the lowest. When people are at the lowest frequencies, they're most easily controlled. Why is social media pushing fear and anger? To keep a population controlled. Everyone has an inner purpose and an outer purpose. The inner purpose is to raise your own level of consciousness. If one person listens to this podcast and their vibe raises slightly, they go out into the world, their vibration raises the people around them, and it escalates. I can't quantify it, and I don't care to. But if I raise my own consciousness, the people around me raise, and they raise around them, and it creates a better society for everyone. I think cryptocurrency and AI together are going to elevate us for generations. If I wanted to get rich in the old system, I'd place myself next to the money printer — the Federal Reserve — and extract as much as I can, which robs everyone. That's how corruption works. In a Bitcoin world, I can't inflate your Bitcoin away. I have to produce something of value for you, and then you send me Bitcoin. So the only way to get as rich as possible is to make as much value for as many people as possible. AI democratizes access to that — someone born in a slum fifty years ago had very little chance; now they have access to all the information in the world and can build a website with Claude. It accelerates following your excitement, and it compounds across two or three generations. ## Web 5 is going outside **Gokul** When you got excited about social media making everyone better, I almost disagreed — it feels like it's brainwashing people and putting them in echo chambers. **Eric** That's a hundred percent true. But technology is inherently neutral. A pocket knife can cut a birthday cake or do harm. Same with crypto, AI, and social media. You can go full doom and gloom — people will be so plugged in, the algorithms will get so good at feeding them content, that they self-lobotomize. But it also spreads good information, and I think the good eventually overtakes the bad because people naturally reject what's bad for them. **Gokul** I feel like AI is going to make people more human because you'll have less to do and more reason to go outside, touch grass, talk to people. **Eric** I look at the internet in stages. Web 1 is read-only. Web 2 is read and write — Instagram, Facebook — but you don't own it; they can cancel you. Web 3 is read, write, and own. Web 4 is the Ready Player One / Matrix thing — crypto, AI, VR. And Web 5 is just wanting to go outside and go on a hike. You have to go through Web 4 to get to Web 5. I get my best ideas outside. I'm blessed to make my own schedule, so I hike as much as I can, film it, and that's where I get the best downloads. ## How we use AI, and token maxing **Gokul** How do you use AI in general? **Eric** AI is a leverage tool. I mainly use it as a learning tool. Most of my focus is on users and partnerships and talking with people, and AI isn't that effective there. The biggest thing we're using AI for right now is Codex — our dev team uses it heavily, but they're the ones architecting it. I use ChatGPT for research and for my own lesson plan — I'll ask it for a fifty-day lesson from a specific person I want to incorporate into my life. Claude is very good for us because it helps us demo the API. When you're talking to someone who wants to build a labor-cohating service, you can show them a live demo instead of just describing it. But you can't force someone to use AI. A trend I disagree with is token maxing — friends at big companies getting judged on how many tokens they use. It's destructive. You're worse than the AI because you're just brainlessly using tokens, and you're training your own replacement — they're analyzing how you use AI and will use it better than you. Recursive AI use is where you get the slop. What really interests me is local models. **Gokul** Have you tried GLM 5.2? **Eric** The Chinese one? I haven't tried it personally. I hear it's almost as good as Fable, a step below. The hardware to run it costs around ten to twenty K. But the direction is clear — people will run their local Cupid from their phone. Google is pushing that with Gemma for iPhones. Local models make the app bigger, but they're more secure and private. I think local models and open source ultimately beat closed, non-local models because of composability. In a closed model, they pay top researchers, but those researchers aren't mission-driven and eventually quit. In open source, I build something great, you build on top of me, and we both get better. Open source attracts the scattered talent and overtakes the closed labs. My prediction: OpenAI and Anthropic know this, so they'll focus on enterprise token sales. ## Bootstrapped vs VC, and what's next **Gokul** Going back to bootstrapped vs VC-funded — bootstrapped companies have that hunger. VC-backed, you're sipping juice in a corner. **Eric** You're weaker with VC money. You have money and connections fed to you, but you sacrifice your freedom. It's like *House of the Dragon* — the wild dragons are more likely to die, but if they survive, they're much stronger. The dragon pit dragons are smaller because they're fed every day. VC has pros and cons. You get media and connections, but a lot of the advice is terrible, and they force you to listen. I've seen it firsthand — they said they'd introduce us to their investor circle if we did X, Y, and Z, but what they wanted benefited their portfolio companies, not us. We did it, and they never introduced us. It creates a conflict of interest between the VC and the startup. When you're bootstrapped, you do things your way. It's harder, but it's more rewarding. VC funding is the quickest way to a quick exit. Bootstrapped is more likely to be long-term. The skill set is much stronger. **Gokul** I think bootstrapped companies have a higher chance of survival over a long period. I call it "seedstrap" now. **Eric** I don't care. It's bootstrap. We just call it bootstrap. **Gokul** Last thing — what are your plans after V2 launches, and what do you see for the next year? **Eric** V2 is scalable and much cheaper — everything is properly developed. With V1 we couldn't afford the profile generation costs, so our co-founder was selling Yu-Gi-Oh cards on eBay to fund it. V2 goes city by city. It's built to get better every day — the more it knows about you, the better it matches you, and the collective patterns across the user base make it better for each person. We're going to keep our grassroots initiative: be friendly, capture hearts and minds, chat with users, spread organically. There's going to be tons of AI slop that turns people off, so I don't think the slop approach works. Personally, I'm excited about the API. We're already getting into hackathons, lots of people want to build on us, and supporting their journey creates a win-win-win. **Gokul** Low key, I might be interested in that API too. **Eric** Super down. Let me know what you want to build and we'll work out a plan. **Gokul** Thanks so much for joining. We call this The Useful Podcast because it's useful in a bunch of different angles — useful for you, useful for me, useful for our viewers. **Eric** It's a powerful relationship. Otherwise we wouldn't do it. It'd be useless, not useful. **Gokul** Being useful is a nice feeling. **Eric** It feels better to give than receive. If you give someone twenty bucks it feels great. If you take twenty bucks from someone, it does not feel great. The same should apply to the content you create — create it with the intention of being useful for others. And like we talked about earlier, that's how you win anyway. --- Back to the [episode page](https://useful.ventures/podcast/eric-mchugh-dataing) · [Dataing](https://dataing.io) · [[podcast|All episodes]]