In short
Podcast Summary: This Week in Startups - Episode E2236
Episode Overview In this episode of "This Week in Startups," Jason Calacanis interviews Thomas McInerney, a renowned angel investor, as they discuss key insights into the startup ecosystem, the importance of founders remaining humble, the evolution of angel investing, and what red flags investors look for in pitches. The conversation takes place during the Founder University in Tokyo, where they explore the key dynamics of the startup landscape.
Key Themes & Discussions
- The Evolution of Angel Investing
- Shifts Over Time: The angel investing landscape has significantly changed over the past decade, transitioning from a more intimate, lower-status field to a highly competitive space.
- Investor Expectations: Investors are now expected to provide more than just capital; they also serve as mentors and advisors to help founders navigate early challenges.
- Characteristics of Successful Founders
- Technical Expertise and Humility: Successful founders are often technical, possess domain expertise, and demonstrate humility. They are willing to listen and adapt based on feedback.
- The 'Idea Maze' Concept: Referencing Marc Andreessen's metaphor, successful founders should be deep into their ideas, understanding various paths and challenges.
- Red Flags in Pitching
- Buzzwords: The use of excessive jargon or buzzwords is seen as a major red flag. Investors prefer clear, concise communication.
- Overvaluation: High valuations can indicate greed and a lack of focus on building a solid foundation with the right team members.
- Behavioral Indicators: The treatment of staff, kindness, and interpersonal skills during meetings can reveal a founder's character.
- Investor Psychology and Market Dynamics
- Optimism vs. Caution: Investors need to balance optimism with realistic assessments. The ability to recognize potential while navigating risks is crucial.
- Understanding Market Trends: Founders should be aware of market dynamics and avoid investing in declining sectors, such as traditional alcohol sales, without a strong growth strategy.
- The Importance of Networking and Relationships
- Building a Community: Successful startups often leverage their networks for introductions and support. Investors appreciate founders who actively foster connections.
- Filtering Mechanism: Investors will often rely on warm introductions and recommendations from trusted sources to vet new opportunities.
Noteworthy Pitches from Japanese Founders
- Sakenomist: A cross-border commerce platform aimed at sake exporters. The pitch highlighted regulatory complexities but raised concerns about the declining market for sake.
- Feedback: Need to broaden the scope beyond sake and emphasize the scalability of the technology for other industries.
- HomiWorld: A social networking platform focused on connecting individuals in real-life scenarios.
- Feedback: Importance of defining a clear target market and understanding the behavioral loops that drive user engagement.
Key Takeaways
- Focus on Clarity: Founders should aim to communicate their value propositions in straightforward language, avoiding buzzwords.
- Understand Your Market: It's essential to not only know your immediate market but also how to pivot to adjacent opportunities.
- Build Trust: Establishing a trustworthy network is crucial for success; both for founders and investors.
- Stay Resilient and Humble: The best founders combine a strong vision with resilience and humility, ready to adapt based on feedback and market shifts.
Episode Sponsors
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Conclusion This episode provides valuable insights into the evolving landscape of startup investing, emphasizing the need for clarity, humility, and strategic networking. Founders are encouraged to focus on building genuine connections and maintaining a clear vision while navigating the complexities of their respective markets.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOUnderstanding Investment Red Flags
0:00 to 0:56
Learn about key red flags for investors and the importance of clear communication.
“So I look for technical founders with domain expertise, generally pretty young.”
Thomas McInerney: Life in Tokyo
2:10 to 4:30
Thomas discusses his move to Tokyo and the appeal of the city for entrepreneurs.
“It's a program you come to for 10, 12 weeks where we work with founders to just go over all the tactics and strategy around building a company, especially in year zero.”
Angel Investing Journey
4:30 to 5:55
Explore the evolution of angel investing over the past decade with Thomas McInerney.
“and it's all these incredible founders and entrepreneurs here.”
The Changing Landscape of Startups
5:55 to 8:01
Understand how the startup ecosystem has changed, including the role of capital and investors.
“And you and I started about the same time, right?”
The Role of Early Stage Investors
8:01 to 10:46
Learn about the crucial role angels play in supporting early-stage startups.
“If you said you were an entrepreneur, especially in Los Angeles, or even in the Bay Area, people were like, ah, why would you do that?”
Evaluating Early Stage Startups
13:14 to 14:01
Understand how to evaluate early-stage startups and what factors matter most.
“All right, we're back at This Week in Startups here live in Tokyo.”
Evaluating Founders in Emerging Markets
14:01 to 16:49
Learn the qualities to look for in founders of new startups.
“or the product's been in market for, let's say, under 100 days.”
The Ideal Founder Profile
16:50 to 18:53
Discover the traits and attitudes that define successful founders.
“When you're talking to the individual, they have deep technical.”
Understanding the Idea Maze
18:54 to 20:28
Explore the concept of the 'idea maze' in startup development.
“I really love this idea that when you're, and Mark looks for this and he's a better investor than I am, he looks for a founder who, they say they're so far into the idea maze.”
Importance of Clear Communication
20:29 to 21:34
Learn why clarity and simplicity in communication matter for founders.
“is super understandable and straightforward to anyone.”
Show all 27 chapters
Navigating the Founder Journey
21:43 to 24:40
Unpack the nuanced challenges faced by founders in their journey.
“When you started saying that, I'm just dovetailing with the maze.”
Signs of a Good Investment
24:41 to 28:00
Identify key red flags and traits that indicate a solid investment opportunity.
“You understand how what you do connects to that big vision.”
Building Networks and Assessing Doubts
28:00 to 30:43
Learn how founders meet influential figures and assess their team dynamics.
“He worked at Uber doing recruiting and at Cloud Kitchens.”
Smart Spending and Founders' Challenges
31:59 to 35:48
Understand the financial pitfalls new founders face and how to avoid them.
“All right, we're back here live in Tokyo for Founder University.”
Optimism vs. Risk Management in Investing
35:48 to 39:39
Explore the mindset differences between founders and non-founders regarding risks and opportunities.
“So ask them, say, listen, I've got some other investors.”
Surviving Market Changes and Serendipity
39:39 to 42:00
Learn how adaptability can lead to unexpected success during market shifts.
“And what you want to do is when we start out, we're just going to stop and all three of us or four of us are going to stand there and you're going to tell me what your line is.”
Navigating Startups Through Crisis
42:00 to 44:35
Learn how startups adapt and survive during crises like COVID-19.
“There's now a bunch of pull in a new way that he couldn't have even guessed.”
Understanding Exponential Returns in Investments
44:36 to 46:40
Discover the complexities of exponential growth in startup investments.
“It's not like in the physical world, the delta between how much we weigh, maybe 20 % or 30 % or 10%.”
Pitch Feedback: Sake Export Business
46:41 to 48:34
Analysis of a startup pitch focused on exporting sake using AI.
“This is why Suconimus is a very unique position compared to other multi-places.”
Reimagining Export Processes with AI
48:35 to 51:33
Discuss strategies to enhance efficiency in export paperwork with AI.
“And anybody who was in venture was like, you can't stop that.”
Introducing Homi: A Social Network Solution
51:34 to 55:40
Explore a new social networking app designed for real-world connections.
“And especially for small business, right?”
Building Community Through Homi
55:41 to 56:00
Learn about the importance of connections and community in social apps.
“And that actually solves that problem for them.”
Exploring Group Activities in Japan
56:00 to 57:20
Learn about the popularity of group activities in Japan and target markets for a new venture.
“who liked to be hosts, and like me, I like to host.”
Understanding Market Dynamics
57:20 to 58:50
Discover insights into market dynamics through examples like Airbnb and eBay.
“I'm very interested in who are the Airbnb hosts of this?”
The Role of Trust in New Ventures
58:50 to 1:01:00
Examine the importance of trust in building community-oriented businesses.
“Yeah, it was like that sort of combination.”
Utilizing Cultural Connections for Growth
1:01:00 to 1:02:40
Discuss how cultural connections can foster community and business growth among expats.
“Now we're going to feel a little bit of heat.”
Innovative Ideas for Connecting People
1:02:40 to 1:03:24
Reveal innovative strategies for enhancing how people connect and experience new environments.
“So that's my strong conviction about how we change the people connect.”
Transcript
Automatic transcript. May contain errors.0:00So I look for technical founders with domain expertise, generally pretty young. They have a point of view about something that they know, that they understand. And normally it's a bit different. Red flags. Top two or three that it's not the right investment for Thomas. Buzzwords. You know, SaaS enabled. When people start using buzzwords, I get, you know, very turned off. I want it in simple English. Because? You're taking too much from the outside world. And those trends are sort of like, you know, fashion. They change daily. And so I think being able to reduce your idea into like a real simple concept that's not using a lot of buzzwords is good.
0:40Let's talk about other red flags. Too high of evaluation. Evaluation in the sense that you just, not to be greedy about equity, but rather to be focused on getting the right people on board.
0:55This Week in Startups is brought to you by LinkedIn Jobs. Post your job for free at linkedin.com slash twist, then promote it to get access to LinkedIn Jobs' new AI assistant. Deal. Founders ship faster on deal. Set up payroll for any country in minutes and get back to building. Visit deal.com slash twist to learn more. Lemon.io. Get 15 % off your first four weeks of developer time at lemon.io slash twist. All right, everybody, welcome back to This Week in Startups. I'm your host, Jason Calacanis, and we are here in Japan for our Founder University. As I explained on the last episode, when I'm on the road like this, launching Founder University, and we now have it on three continents in three cities, the United States, occurring in San Francisco and Austin.
1:45We have it in Saudi Arabia, in Riyadh, and now we have it here in Tokyo. That's enough work. We're not going to launch three more cities because I got a family to raise and I've got a portfolio with hundreds of investments in it. We're really excited about the program. If you want to learn more about the program specifically here in Tokyo, go to Tokyo.launch.co and you can apply for the next one we're going to do probably in the summer or in the fall. And if you want to learn more about Founder University, which is a pre-accelerator. It's a program you come to for 10, 12 weeks where we work with founders to just go over all the tactics and strategy around building a company, especially in year zero.
2:23About half the companies who come to the program are not yet incorporated. They're just projects. They're MVPs. They're business plans. They're vibe-coded little prototypes. And we love that because that's where founders could use a lot of help in learning how to pitch their product, how to go to market. And today we're going to talk all about that with a good friend of mine who is making his third appearance on the program. I can't believe it, Thomas. Thomas McInerney is an angel investor extraordinaire, and he now actually lives here in Tokyo, correct? Yep. I mean, maybe the most livable city in the world, don't you think?
2:58The cleanest, best food. Safest. Everything is fantastic here. I love it. I mean, you see six-year-olds walking to school by themselves. It's unbelievable. My nine-year-old daughters, my twins, were absolutely flabbergasted about that. And I saw all these kids walking to school with their backpacks. So cute. So cute. And everybody has the same backpack. Yeah. So then I worked backwards with some of my founders here. I said, where do we get those backpacks? Peter, I asked some Grok and ChatGPT, where do you get them? I figured out where you get them. And I went and I bought my daughters these with all the stickers.
3:28And now they bring them to their school with them. That's awesome. Yeah. They're special backpacks. They're very nice. They're not just, you know. Unbelievable. Yeah. All right. So let's get started here. You've been an angel investor. Well, let me ask you before we do that. Why did you move to Tokyo? I, like you, lived in California for a long time, about 25 years. During the pandemic, I lived in LA. I was in Santa Monica. Conditions got pretty rough there, as you know. It was pretty frustrating. A lot of people moved during the pandemic to various places. And we moved to London. And we lived in Chelsea.
3:57We evaluated three cities, Tokyo, Miami, and London. We chose London. And we were there for about three years. and then they changed the tax policy in a big way on us. They got rid of non-DOM, which is kind of, they used to not tax worldwide income. So anyway, and we'd love Tokyo to begin with. My wife's Japanese. So it was a good excuse to come here. We've been here about a year now. And you're not the only one. I won't say who else is here, but we had a lunch when I was here in the fall. And I was just delighted to have a dozen of you show up for lunch with me. and it's all these incredible founders and entrepreneurs here.
4:35Why do you think entrepreneurs and founders, especially successful ones, wind up here in Tokyo? I think if you're, from a pure lifestyle standpoint, Japan, like we kind of covered a minute ago, it's so hard to beat. It's clean, it's safe, it's cosmopolitan. You can be anywhere and generally one flight, certainly one stop anywhere to anywhere in the world. It's got skiing, it's got culture, it's got incredible food, more Michelin stars in Paris, and on and on and on. So I think it's one of the most livable cities. I think the tech ecosystem's new, vis-a-vis Bay Area and other places that are more developed.
5:13But there's a lot of interest at the government level, and we're having dinner with some of those people, and Jetro is sponsoring this event. So I think the government's backing and putting capital and effort into supporting tech. So I think it's a great time to be here. Yeah, it's a fantastic time to be here. So let's get into, even before you were an angel investor in incredible companies, Notion, Segment, man, both of those companies, fantastic. And then even some that were very promising early, but then had some challenges. Bird and Clubhouse come to mind, and you started doing some late stage.
5:46You got SpaceX in there, Uber, yum yum, OpenAI, Anthropic, and Perplexity. So you have really run the table. Total number of investments you've done? Probably about 130 or so. 130. And you and I started about the same time, right? Like 10, 12 years ago? That's right. What was it like 10 years ago in the United States when you and I started angel investing? And then how has it changed in the last decade? So definitely, and it might be more than 10 years. My first deal I saw, which is the one that haunts me to this day, was Airbnb. My lawyer incorporated them, a guy named Michael Blum. And I saw it at like two and half before they went to YC.
6:21So that was probably, it's like 2009, maybe, something like that. Anyway, you know, when I did segment, for example, it was Y Combinator was itself brand new. There were like 30, you know, metal chairs that were folding chairs and Paul Graham, we'd also, he would open them up and Paul Graham was running it and I did segment at a$5 million valuation. So YC deals were priced that way, so much cheaper. There were fewer of us back then, as you know. We were trying to build syndicates before syndicates existed. Exactly. Just so we could get 10 people to give 25 or 50K each, just to give the founder enough money to get to a proper seed round and be ready for a venture capitalist.
7:03Exactly. And you did the Sequoia Scout Program. I think that was the first VC Scout Program. It was. So all of it was getting built. All of it was new. And that was, to me, a super fun time to be in the Bay Area. It was awesome. And there weren't as many startups. and the people who were choosing to do startups were of incredibly high caliber and you had to be a bit resilient and a bit of a maniac to do it, yeah? Yeah, I think there was, you know, now it's actually, you know, prestigious or sort of, you know, understood. But back then there was a lot of authenticity just because it was a smaller universe of people, people that were really in it and doing it because that's what, you know, they didn't know anything else.
7:46Now, you know, everybody, you know, after Facebook and, you know. The social network movie. Exactly. It's, you know. It's high status in a way. It's a high status thing. You know, it's almost like being in a movie business or something. So it's changed. And it was low status when you and I started. If you said you were an entrepreneur, especially in Los Angeles, or even in the Bay Area, people were like, ah, why would you do that? Yeah. Sounds painful. You're a misfit, right? Well, yeah, certainly in the Bay Area, I think that it was cool, but it was hard. You know, there weren't the rails. They hadn't been built out, the YCs.
8:22You know, it was much harder to raise money. Angelists, syndicates, even angels. Exactly. When I started Open Angel Forum, I think I got to maybe a dozen people, two dozen people in the major cities. But it was hard because there just weren't that many of them. No, no, exactly. Exactly. You know, our friend of all, our mutual friend, you know, he got AngelList going, which kind of created a little bit of a good ecosystem for investors to connect. And like you say, cobbled together enough half a million, a million dollars to sort of start a company. And at that time, we were very coveted as early stage investors.
8:56It was like, I really appreciate you. When so much money came into the system and YC, in some ways a victim of their own success, because so many people want to go there with status that it became a bit of a competition to see and I've got to be you know judicious here with my comments but I think the posture changed from wow these angels really are angels in that sense they're putting their money on the line they know it's a 90 % chance they get nothing back to hey how can we manipulate a bunch of dentists and high net worth individuals to come to a demo day create scarcity and it became very pushy and gamed a little bit yeah yeah and even venture itself the VC star pushing into earlier and earlier as well.
9:36So it became definitely for us now, I think money, being an investor is a commodity. So you definitely have to provide more than just money. You really have to, which is what you're doing here. You have to help the founders really fundamentally. You have to build a reputation over time. There's a lot you have to do and it's competitive. What do you think on our best days, angels, those first couple of checks, the first 10 investors before a proper seed fund comes in. What do we do really well? And why were we coveted? Still coveted. But what do we aspire to do in those, that year zero, that year one?
10:14Yeah, well, number one, don't get in the way. Don't be a pain in the ass, which is sometimes underrated. Hopefully you give some bona fides and you give some credibility. When someone's starting out, as all of you know, the hardest thing to do is you're young, you're not well known, you don't have any traction. So you're trying to just develop a reputation and get people to pay attention to what you're doing. So part of it is, hey, Jason's an investor in my company. Oh, Jason. Oh, J.K. Ellis. And Thomas is also in. And now Sokka's in. And Naval came in. Boom, boom, boom. And that momentum is in a way, it's kind of like building consensus.
10:54And it's a filtering mechanism. Right. And when you look at VCs, they're so busy, they have to put so many large chunks of work together that they really do appreciate. Sometimes they don't always show it. And they try to, the bad ones try to run over the angels and maybe take away their rights or, you know, whatever it happens to be. We've got some good war stories there we'll get into. But they appreciate that filtering mechanism. Yeah, absolutely. I mean, even me, when I look at my inbox, I'm looking for a reason to delete an email. you know every email I'm thinking how can I delete this because that's one less thing I have to deal with yes and so even you know cold intros it's so much better to get a warm intro which your early checks can provide because that filtering mechanism is strong and so the curation piece which is what you're saying you know as curators say hey we we met this guy or girl we like them we think they're good we think this is an interesting space and so take a look all right when we get back from this quick commercial break, a little pause for the cause, and we do cover our sponsors here at This Week in Startups.
11:57I want you to take me through your rubric, your heuristics, your rule set for companies that you absolutely have to invest in, and then also your turnoffs, things that are red flags that you will never invest in when we get back on This Week in Startups.
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13:29Excellent. We have about 50 founders in the room representing 30 companies here. Most of them are first-time founders. When we meet with these companies, we like to assess what they need help with. Number one, number two is almost, well, top three. How do I raise money? How do I get you to give me a check? Number two, how do I find a co-founder? Although if they're here, we've already sorted for that. And then typically the third thing is how do I get my customers? How do I go to market? Let's start with how you look at and evaluate an early stage startup, one that either is about to put their product into the market or the product's been in market for, let's say, under 100 days.
14:07You don't have meaningful data to review. It's all about the founder, as you know. And so I try to take a very close look. And that's been what I've been good at and my secret sauce. These markets change super rapidly. When I hear guys like David Sachs or, you know, was it Thomas Tungs, the guy that writes the… Yeah, Tungsin, yeah. You know, that has these. These guys are really smart about an ecosystem. Those SaaS has just changed. But it's continuously changing. So my strength was not mapping out that topology. It was rather kind of human profiling and looking at a founder and saying, hey, is this the person that's going to get it all the way across the finish line?
14:45So I look for technical founders with domain expertise, generally pretty young. They have a point of view about something that they know, that they understand. And normally it's a bit different. I'll give you an example. I did Radiant Nuclear. I went to see the founder a couple of days ago in El Segundo. He told me, I actually didn't realize that I was his first check. So, you know, they're just raising$350 million right now. Tim Draper at close to$2 billion. dollars when I did a nuclear company this was you know I can't remember maybe six years ago nuclear was not in vogue I mean nuclear was dead it was dead it was that would be a fool's errand because we hadn't built one yeah since I don't know if 70 or 73 exactly we had we have a couple of plants where we might consider building one but after Fukushima after Three Mile Island and after Chernobyl after those three yes this fear of like oh my god this is terrible so you then I I'm guessing, had to figure out why this would be different.
15:46Yes. Why was it different? So the founder, Doug, I had always been drawn to deep tech companies. So super technical founders. You know, Segment was three MIT dropouts and another guy. So I liked, I've had a propensity to bet on technical founders. This guy had worked directly for Elon on some projects at SpaceX, had been there a long time, super bright guy. And he ended up raising, I remember, the Series A from Andreessen and Union Square. And I was shocked because I was like, nobody was, they weren't doing those kinds of things back then. They were doing more sassy software kind of stuff. So in my case and in the founder's case, you have to be different, right?
16:28If you're one of 100 entering some crowded space, like, you know, say LLMs now or, you know, AI coding or something, it's going to be super, super hard. So you have to be weird. You have to be different. And there has to be some thesis of why you're going to disrupt a space where there's some number of incumbents. Exactly. Yeah. Let's unpack, double-click on the individual. Okay. Technical. Yeah. What else? When you're talking to the individual, they have deep technical. You said young. It is a young man's game, a young person's game. To use non-gender specific language, it's a young person's game.
17:03I think most people agree you have to do a lot of sacrificing. Although the returns for second and third time founders are really good too. But we do see that sort of dichotomy. Either it's Mark Pincus on his third startup or Elon on his third or fourth. Or it's somebody right out of college or just dropped out. Right, exactly. But unpack more of the, if you can put your finger on it, the personality type. Not that we want people here at Founder University to be inauthentic. Yeah. But I'm just curious what you've learned. I've found that they're humble but smart. So they're listening. They're not defensive when they're, if you ask them a hard question.
17:41like why this why that there's no defensiveness or even even if you say i don't think this will work for this reason they don't take it personally they kind of process what you're saying and then sort of you know have a counterpoint so you have to have this kind of crazy confidence to to bet on yourself and think you're going to disrupt an industry at the same time you have to have a certain humility to take feedback and respond to the universe when it's telling you something's not going right. This is super interesting, I think. I call it internally at our firm, like, is it enjoyable to volley, to play tennis, to play ping pong, pickleball, whatever it is, with the founder?
18:16A founder, when you ask them a tough question, hey, there's seven other LLMs, and now there's 15 open source projects, how are you going to cut through the noise? Now, some of them might just be like, well, we'll be better. And you're like, okay, can you explain to me how? And if the person is just filibustering or it's not credible and they're not asking you questions and it's not that productive discussion. You're like, wow, I wonder how this person is going to hire people, find partners or raise money from a series A firm. They need to have that humility to engage that discussion, but also that confidence of you, we're going to figure that out.
18:52Exactly. Mark Andreessen talks about this, the idea maze. I really love this idea that when you're, and Mark looks for this and he's a better investor than I am, he looks for a founder who, they say they're so far into the idea maze. So when you talk about an idea, their idea with them, you can see that they've tried this, they've tried that, they've thought about it this way, they've thought about it that way. They are so deep in it that when they're talking to you, it becomes immediately clear, or should be clear, that they don't have all the answers, but they know what they know well. It's such a great metaphor because if you think about it like the maze from The Shining or any of those kind of mazes, like the hedge mazes or the ones made of hay, if you were to just, while they're talking, it's almost like you see it being drawn and you are pulled up to the three-quarter view and you look down on the maze and you're like, oh, I see, yes, dead end, dead end.
19:47The mouse is looking for the cheese. Oh, yeah, you figured out two-thirds of it, a third of it. You're ahead of everybody else. And they'll take you through that. A good founder will take you through that. Even Dog with Radiant, I'm certainly not a nuclear expert. I'm a generalist, but I started asking questions and it became clear, you know, well, the neutrons will hit this, this thing and do this and do this, and then this will happen. And then the design of his reactor, there are small kind of rice size pellets surrounded by carbon and so that they can't go critical. And he broke all those pieces down for me in a way that was understandable.
20:19That's another thing about Elon that I think he's probably the best in the world at is taking really complicated things like rockets or, you know, self-driving cars or whatever it is, the physics of a battery in cars and breaking that down in a way that is super understandable and straightforward to anyone.
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21:26That's why more than 37 ,000 startups and fast-moving companies are already using Deal to accelerate their hiring and growth. Find out more by visiting deal.com slash twist. That's D-E-E-L dot com slash twist. It's really interesting. When you started saying that, I'm just dovetailing with the maze. I remember sitting there with him when we both lived in Los Angeles and we had some of the first roadsters. And we were talking about batteries and consumer behavior. And it was like, okay, this thing can do like 180 theoretically, but I'm getting more like 90 miles. That's fine because I'm driving to Culver City from Brentwood and you're going to SpaceX.
22:10But how is this going to work out? And he said, well, we have this idea of you're going to be able to drive when you're going cross country and there'll be superchargers and we're going to have these ones that go much faster. Then we're going to have the ability for you to go in, undo all the screws, the battery will drop out, move over and we'll slide it up. Yep. And it'll be one of those two. And then we're going to have these at your office and we're going to subsidize people to make it a destination. So having a charger will get you those customers who have the$150 ,000 car. Yep. You're a hotel.
22:40You're going to love that. And all of a sudden, as I'm saying this, this is, how old is the Roadster? 2013 or 14? Maybe we'll have a look it up. It was incredibly early. It was 2006 when I got mine. Oh, my God. It's been 20 years. I had Roadster number 633. Do you know your car number at all? 16. Wow. Who knows my car number? 16. But we were some of the first, and that car was dangerous and fun and exhilarating. and crazy, but he was going through the idea maze. And I saw a similar thing with SpaceX. People don't know, but before SpaceX, his idea was he wanted to back up the biosphere. So he's always been thinking about not Fermi's paradox, but there's another, I remember at some point he said, how do you think the world ends?
23:27And I said, meteor or pandemic? He's like, oh, that's exactly what I think. Number one and number two. And then I was like, yeah, or nuclear holocaust. He's like, yeah, that's number three. We were going through this idea maze of just how does the world end? And his idea was to build, like the movie Silent Running, great 1970s fiction film with Bruce Dern, to put giant biospheres and send everything up there, like those seed banks, but put it all up in space. And he's like, he went to see the Russians. To buy a rocket. To buy a rocket, to do it, or buy a carriage on the rocket. And then he realized, oh my God, maybe I should just build the rocket.
24:02So biosphere to rocket, and then Starlink. Yeah. You know, it's very interesting. like unbelievable unbelievable and you don't know all the and even someone like elon who's super bright and wrote writes out the master plan you don't know all the answers but as you move down the road you your headlights shine that much further and you can and then you can start to work on the next set of problems so you're sort of like keeping this mental kind of north star and then you know okay but there's a storm so we're gonna have to take down the sails we're going to have to so you're you're kind of continuously adjusting and and responding while ideally having some big vision which he's done and then he he did also a super good job connecting his employees motivating them with you know even like you know i make the screw for the fin that gets the rocket into space so that we can put you know mankind on mars but it all it you Even if you're working on a screw at SpaceX, it rolls up to the mission.
25:04You understand how what you do connects to that big vision. At Tesla, it was to make sustainable energy in addition to the electric cars. The electric cars were the way that the battery packs, the solar, all of that would manifest itself eventually. And then FSD sort of became his obsession as well. So you're looking for those founders, and I'm assuming also a level of work ethic, resiliency, where that mission kind of drives you to wake up every day. And when you do that 12 or 14-hour day, and you do it for 100 days in a row, and nothing goes right, you don't quit. Yeah, it's very hard. It's very hard.
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25:45I mean, you've got to love this business. And we were talking about Elon. People talk about Steve Jobs. I worked at Apple in the 90s when he'd come back. You study the greats, right? If you're in this business, you look at, you know, it's like studying a football player or a soccer player or a tennis player. You know, you watch hours of footage. You hit, you know, hundreds of balls or kick thousands of balls. You know, you're just every day you're in it. Eventually, over time, you make progress. Okay. Red flags. Top two or three that it's not the right investment for Thomas. Buzzwords. You know, SaaS enabled.
26:20When people start using buzzwords, I get, you know, very turned off. I want it in simple English. Because? Because I think that you're taking too much from the outside world, and those trends are sort of like fashion. They change daily. And so I think being able to reduce your idea into a real simple concept that's not using a lot of buzzwords is good. And let's talk about other red flags. Too high of evaluation. I don't know. Yeah, valuation in the sense that you just, not to be greedy about equity, but rather to be focused on getting the right people on board. And if you do that, everything takes care of itself.
27:01If you make something big, whether you own 10, 20, or 30%, it won't matter. Especially in the first company. Yeah, yeah. This is a secret that I normally don't share, but I will for you since it's a good opportunity. I take people out to typically a lunch or breakfast, sometimes dinner. and then I see, are they kind to the staff? Are they kind to the waiters? What kind of human being am I dealing with? Just their little tells like that, little poker tells that you look for. Yeah, that's a great one. The ability to also hire and inspire, that's a really important one for me. Key. Key. How do you suss that out?
27:37You know, when I ask to meet the team or hey, let's have my team meet the team and just, hey, why are you here? What did you do before this? If you look at the pedigree and how they found the person, and hey, how did you meet Jason? Or how did you meet Elon? And it's like, I emailed him. You know, if you were to ask Travis, and we had somebody who worked for Travis at both Uber and show yesterday spoke. He worked at Uber doing recruiting and at Cloud Kitchens. And I said, oh, how did you wind up meeting him? And he's like, I emailed him. You know, I gave him some ideas. And then when he was doing Cloud Kitchens, I emailed him again and he responded.
28:12And how you meet the person, I remember talking with us back to Elon and just some other folks. They typically, it's really weird, but through social media and through their network, they just meet smart people. And they really are good at assessing that. And then they're also really good. I remember we were, Elon was struggling with who was going to be the CEO of Tesla when he, you know, started investing in the company. And then he had to fire a bunch of people. I said, oh, you seem like you have a lot of doubt about this. I said, yeah, I got a lot of doubt. And I said, yeah, what are you going to do?
28:41And he's like, I've been struggling with that. And he said, but at the end of the day, if there's any doubt, there's no doubt. and that was like opened my brain up and he had heard it from somebody else in silica valley but when you have these doubts about somebody on the team yeah as a founder you're a hundred percent right there's never a chance where you're like this person's not the right person i need to get rid of them it's only how quickly do you do it yeah yeah it's hard it's hard to do that but it's better to fire early because you're setting your culture right so when you have the the early founders and bad people in the culture will be rejected almost like an immune system in the body where if someone is not the right fit, they will be.
29:17So it's super key to get that DNA set early. I also think about that when I ask them another secret tell kind of thing is when I ask them, tell me about your first three customers. And they're like, well, we sell into the military and we sell into this. I'm like, yeah, okay, tell me the top three companies, the one you landed first, the second one, the third one, how'd you get them? And sometimes we'll get that during the due diligence process. But a lot of times they're like, yeah, The first two are my friends from college. They're my fraternity brothers. And they did it for me as a favor. But the third one I reached out to through LinkedIn.
29:49And then they didn't respond. So I cold emailed them. And then I met the next three at a trade show. I went, what trade show? They're like, oh, yeah, there's a trade show for lawyers in Milwaukee. I went out to it. And I just couldn't afford a booth. But I just intercepted people at coffee. And I introduced myself. And I got three customers there. And you're like, holy cow, this person is like, you know those dogs that hunt for truffles in Italy? You ever go on one of those truffle hunts? Yeah, yeah. It's wild to watch these dogs. They just, all of a sudden, they just run away, and then they're just pointing and scraping at the bottom of a tree, and then there's five truffles there.
30:18They're like those truffle hunters. Yeah, yeah, that's right. Because that understanding of your customer is super key because it rolls into the product, right? You've got to be, you have a tight loop between how your customer is using the product and how the product is evolving. When we get back from this quick break, I want to ask you, what should founders do with that first$250K,$500K in year one of their startup? Let me get back on this week in startups.
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32:11They've got it deployed. They get into an accelerator. They get another 250K, whatever it happens to be, 125K. What are you trying to accomplish in those first 12 months? Well, don't blow it. That's the first thing. Burn rate is interesting. You would be shocked. The number of companies that I've been an investor in that have gone wrong from overspending, it is crazy. And even one I have now where it was going to do an acquisition. It was a big company. It raised hundreds of millions. The partner on the deal had a medical problem, a serious medical problem, dropped out. They had already signed to make the acquisition.
32:45so i've seen every permutation of companies running out of money so i know it sounds like obvious or pedestrian but really do not run out of money you know and it's pretty rare where i've thought oh these founders are too cheap you know get crappy furniture get a crappy office frugality matters frugality matters frugality matters the way i've said it internally is we're looking for founders who get a dollar of value from a nickel, not founders who get a dollar of value from a hundred dollar bill. A hundred percent. And yeah, when you get that money in the bank, sometimes you just do stupid things.
33:21I had one founder who hired a PR firm because people had told him and I said, how much did you pay the PR firm? I said,$35 ,000. And he had raised like 2 million. And I'm like, okay, yeah, you got to stop that. We don't need that much press. And it's like not important. And he's like, oh, I signed an 18 month agreement. I'm like, okay, I'm going to call them and read them the riot act. And I got them to settle to get it out that to get them out yeah but it was pretty brutal have you seen a company with a lot of money in the bank go out of business yeah oh time and time again right no no company with a lot of money oh right right right no no exactly yeah yeah that that is your that is your oxygen i mean that is like you're in an airplane that is your gas you know you run out of gas the plane is going down you cannot run out of gas you cannot spend your money you know to the end and you and you cannot investors, they'll string you along.
34:08Who knows? I've also seen real misconceptions between where the founder thinks they are in a fundraise and where they actually are. How do they go from saying, okay, I'm about to close this million dollar seed round and you know you're not even close. How do you advise them that you may want to cut half the staff or get everybody to reduce their salaries and take your three months of runway to nine so you have more time to close this because I don't think you're going to close it. You're not going to make it. That's very hard. It's very hard, but they got to do it. You just make the tough decisions.
34:44Ideally, you don't get your burn up that, you know, you're always thinking like, how many months left do I have here? How many, you know, I've got 24 months of runway, we call runway, right? 12 months of runway. And where am I going to, what am I going to accomplish in that time? So runway is super key. Money in the bank is super key. And then the milestones you're going to hit, you know, where you think, okay, I'm going to, cause you're also looking, I mean, look, once you reach product market fit, there are all kinds of guys show up on your door to help you and give you money. Right. I mean, not only just, you know, investors, but also, you know, employees, right.
35:21If you are, if you have a product market fit kind of company, things get a lot easier, but that, that initial, you're drilling for oil, you're wildcatting, you're sort of landmanning. You need to drill as many holes as possible to figure it out. Running out of money is just brutal. So unfun. I tell folks who are like, oh my God, I've got this one person they've committed. And I'm like, okay, can I see the term sheet? We're like, oh, we don't have the term sheet, but they gave me a verbal. I'm like, okay, anything that's not a signed term sheet is a no. So ask them, say, listen, I've got some other investors.
35:54We talked about some broad terms. Would you like to send us a term sheet or should I send you the term sheet? And just be a forcing function. And then if they don't send you a term sheet, when they say they're going to, they're out and proceed as such. And you have to, I mean, in a way it's like ball control or pot control in a poker game. You have to control that process. What is a great fundraising process for a company that doesn't have a hockey stick? And find out what they need to get to that term sheet. Like, okay, I need X data or I want to talk to these three customers or what, what is it they need to get there and ask them really, because they'll share that normally unless they're being really cagey or just keeping, you know, being, I think a good investor will be super candid about a, if they're in or not, like you say, but you've got to kind of really put them, you know, put their feet to the fire and then B if they're almost there or not quite there, what they need to get across the way.
36:50How do you say that to them? Say, what do you need to get to a yes here? Or what do you need to sign the term sheet? What do you need to see from me? And that makes your job a lot easier because a lot of the challenges is communicating what your value is. And people have different things. You may want to see something different at Founder University than I do. And some people might not do reference checks and not even do due diligence. And you're like, okay, well, what's the holdup here? And that's where forcing them to get it in and get that term sheet in and sign it and tell them the timeline that you're doing.
37:22this on. For example, let's say I was raising my, you know, Jason, you said you were going to do, you're interested in about a 200K check size. Is that right? You know, you need to take notes even in the meeting and say, okay, and then what's the timeframe in terms of closing this? You need 30 days. What's your process like? Well, Tom, we need to look at, you know, we need to speak to three customers. We need to look at your code. We need to da, da, da. So that your investors will generally and your customers too, they'll tell you what they need. It's up to you if you ask the issue, if you ask.
37:50And I think maybe some first-time founders are like, wow, I don't want to push them. You actually, they want to be pushed. They want to get this decision made. And sometimes they're just busy. They have a life, these investors. Maybe they are dealing with other issues in their personal life or in their firm. Exactly. There could be dynamics going on you're not aware of and pushing that issue. What do you wish you knew now with 100 investments that you didn't know then? I wish I had been more aggressive. I think I'd taken more risk. For example, Airbnb, I overthought it, you know, it was a second angel deal I'd seen.
38:25So I should have just done it. And I was even, didn't even know how to do the docs back then. And, you know, should I get my lawyer or should they, this is even pre-safe notes. Safes had just been kind of - Yeah, it was back in the convertible note days. Yeah, yeah, yeah, yeah. And it was early. And so take more risk, be more of an optimist. You know, I think that's something Mark Andreessen is super, super good at. He's still good at it. I heard that they raised such big funds. People were like, you're going to have to return like$600 billion or something to, you know, or you're going to have to have$600 billion of outcomes or something.
38:56They did it easily. They cleared it. So being an optimist, I think, you know, even AI was quite bullish on AI, but I should have bet bigger into the AI trend. Are you conservative by nature or are you cynical? Have you been burned? Why were you not as aggressive, you think? Was it fear? Well, yeah. You know, when it's your own money, I haven't dealt with, I haven't generally, I've done a few SPVs, but generally I bet my own cash, which is different to most. You know, when I was starting, I thought I need to learn, but there was, that was such a good time. Right. And I bet five years from now, 10 years from now, we're going to look back and we're going to say, this was such a good time.
39:33Right. You know, we might say like, this was such a good time in Tokyo. It was brand new. The ecosystem was just developing. You remember Jethro is holding events in the Arc Hills and you know optimism is key optimism is important there's this great expression that they tell drivers you in race cars look at the track not the wall yeah yeah cuz you look at the wall you drive into the wall that's right you follow the track and I was teaching my daughters how to ski through trees and they love it it's her favorite thing to do a ski through trees yeah mom's not as excited about it as we all are they said well how do you not hit the trees I said don't look at the trees look at the space between the trees.
40:12Yeah, look at your line. Find your line. Yep. And what you want to do is when we start out, we're just going to stop and all three of us or four of us are going to stand there and you're going to tell me what your line is. You're going to point to it with your pole and draw it for me. Think about it. Visualize it. And how many turns is it? You're like, well, I'm going to make like a couple of turns. Nope. One turn here, one turn there, and then you're going to go straight and you're going to pick up a little speed on that straight one. But the speed's okay, but you're not going to look at the trees.
40:38You're going to look at that space. what do they call it, the negative space or something? Right, right. Between the trees. Yep. These girls can ski through trees like you wouldn't believe. And I think that's in some ways what we all do as investors and founders, which is like, you make this big long list. Yeah. These are all the things that will go wrong in a nuclear startup. Right. What could go right? What's on that list? That list is like two things. Yeah. Three things. Yeah. The list of what could go wrong is 300. Yeah. If you over optimize on that, you will talk yourself out of every decision.
41:06Yeah. Yeah, I think, just to your point, it's a super, super point. Like the founders, what we noticed in companies was a founder versus a non-founder is the mind of a non-founder goes first to the risk. First to why it's not going to work. First to what can break. Whereas a founder sees that opportunity and then they're like, okay, these challenges are risks and I can manage them or I can deal with them. But they first go to the opportunity versus going to the risk. What if you could? what if small modular nuclear reactors worked? What would that look like? Yeah, exactly. And then if you stay around, the longer you're alive, and this is back to burn rate, the more chance you have to get lucky.
41:47I mean, now for Radiant, there's such energy demand due to AI. There's no way Doug predicted that, but he knew that energy was important and the demand was compounding. And so now he's in a super lucky place. There's now a bunch of pull in a new way that he couldn't have even guessed. It is a really interesting thing that happens. You have something like COVID. And if you're Airbnb, you just totally get your ass kicked. And you have to figure out how to survive. If you're DoorDash, all of a sudden, everybody's like, hockey stick. Like, how do I get food to my house during quarantine or Instacart?
42:23And people are like, I'll take the 15 minutes to figure out how this works. Exactly. And staying alive to do that is the key. Yeah. Yeah, a friend of mine, a guy, Adam Ross, you may know, a super guy, has an expression. It's like, if you hang around long enough in Silicon Valley, you get hit by the money truck. And so, you know, hopefully... You're looking at me in a very targeted way. Both of us. Well, I mean, even for investors, that is key. It's so key as investors to get lucky. And if you make a certain number of bets and you don't give up, you will eventually get lucky. It's just somewhere around the 20th or 30th investment I find something breaks for an angel, for a seed fund.
43:08But you have to, talking about our business, if you only do five investments, man, the chance is hard. How long did you know before you got the sense you were good at this? Actually, the one thing about Airbnb was every time I'd go to the airport, they'd be on the cover of some magazine, the guys. And that was like, you can only lose one extra money. You learn this later as an investor, but you you you know if you miss out on a thousand X or ten thousand X and Maybe the case of Airbnb that kind of said hey, you know, I was like wow I had miscalibrated my risk, you know This is so key the human brain has a very hard time Understanding the concept of a thousand X It's just so exponential and it doesn't exist anywhere else in finance when you get your credit card bill if you don't pay it and they charge you 2 % that month or 30 % that year, you're okay.
44:00And then if you buy a stock and it goes 5X and you went 500 % in five years, you're like, oh my God, this is incredible. And when I talk to people and they talk about the Uber or the Robinhood investment, I'm like, yeah, 1 ,000 and 7 ,000X and growing. And I still haven't sold any shares of Robinhood. And I paired my Uber position early to Masayoshi-san had some shares to buy. We all did. But I haven't sold any since. I'm like, wow, that is a very bizarre thing to have a 7 ,000X or 1 ,000X. And all the compounding, the doubling at the end, and one doubling at the end is worth all the multiples up until that point.
44:33So Buffett was extremely good at understanding compounding. You're right. It's not like in the physical world, the delta between how much we weigh, maybe 20 % or 30 % or 10%. It's hard to think in these orders of magnitude where, you know, the startup world and the tech world and certain things don't run that way. They run in like exponents and they run in a different kind of math. If you were in a poker game and there were nine people in it and they each put$10 ,000 in and you somehow figured out how to take everybody's money in a cash game, you would make nine times$90 ,000. Exactly. Now imagine a poker game where you put the$10 ,000 in and you made a thousand times it and you're like, how is that even possible?
45:11It's a hundred other poker tables. Yeah. Worth of players. $10 million? No, more. I think it's a hundred million, right? So a thousand, thousand would be one million. No, it's 10 million. You're right. So it's like, how did I put$10 ,000 down and make$10 million? It doesn't make any logical sense. Yeah, exactly. Pretty amazing business. Yeah. Thomas, I asked if you would be so kind as to take very raw pitches from these year zero companies. Thomas and I will do a couple of pitches and we'll just give some candid feedback. Sure. Sounds great. Hi, everyone. My name is Hiroshi Takeuchi. I'm a founder and CEO of Satinamist.
45:43We offer AI native cross-border commerce platform for sake exporters. So here's the customer. Mai, she's the first Misesake, and she's the owner of Sake Export Business. She has some problems. One of them declines Sake Burearies. Due to the decrease of domestic consumption, it will improve that. She needs to enhance export capability. However, it's a lot of paperwork, and then it includes documentation and language barriers. This is why we have a solution, Sakeonomist. Mai, she uploads the product documentation to the cloud, and then in back-end part, validation check is executed. And once it's done, she creates the content on top of that, then publish, and then sell it to the importers.
46:26Then once purchase has been placed, and then she can ship the documentation to the country selected, and then she can trace in orders, you know, what's going on in the order. As you can see, the operation is quite complex and has an industry-specific requirement. This is why Suconimus is a very unique position compared to other multi-places. And then GDM strategy to brand as an alternative wine and then brand into Dubai in the southern US. And then create a new segment aged sake as new asset class. Business model is get transaction fee from the importer's payment to the exporters. No initial, no license cost.
47:03Then we have some government subsidy in the past. And then we identify customer right now. Then we are looking for the importer now. Opportunity one segment is vertical right now. But we have a playbook. we can extend to the other regulatory commerce in the trade. We have a team here, myself, and a tech lead in Masami. We have spent open source in the past, in 10 years. Then we have a GTM advisor, Katsu. With this team, we are going to promote Japanese culture and spirit to the world. Thank you for listening. What are your first thoughts? Key, key point you showed in near the end. Sake is not a big enough vertical of investors, especially the later stage guys like the Series A and Bs.
47:41they're going to look for huge Tam. They all care about Tam. And so I like the idea of starting with a vertical you understand, like sake. And then there's, you know, Indians importing, you know, a certain type of curry to, you know, to Japan or to Dubai. So I like the idea of this going beyond the sake vertical into many, many verticals. And it's really about exporting from one country to another, any kind of product. And it sounds like the regulatory piece is the hard piece, certainly for alcohol, but probably any kind of, really probably anything nowadays, there's a lot of paperwork. So to make this a really big business, if you're good at doing that, I think it's a really good idea.
48:22Thank you. And this was exactly what I was thinking. And we both kind of looked at each other when you showed the other verticals, because I was thinking, wow, this is so niche and it's a declining market. There was a time when the newspapers were declining and everybody was building tools to help newspapers stop declining. And anybody who was in venture was like, you can't stop that. So you're essentially selling into the Titanic that you want to sell ice cream on the Titanic. And it's like, yeah, the Titanic's going down. There's not another voyage. And you tie yourself to it and it goes down.
48:53So you present it as your first market, a market in decline. And we're thinking, yeah, people stop drinking. People are on Ozempic. Like you want to find a beach where the tide's coming in not going out so this pitch had all these signals of no no no no and that at the end it had the yes oh he's going to do it for these other verticals but the name also then you're trapped in the name so i want you and i'm going to give you permission to think big you have my permission so you're now allowed to do it yes yes ditto on the name yeah i was thinking that you could have this name and then do other names but i think try to make more of a general name and this is maybe be all super clear in your head, but for investors, they need to know this is super big right from the start.
49:37And you did explain the problem really well too. So we can fix this. You said, hey, look at all this paperwork you have to fill out. And it's very regulated. A lot of paperwork. This is a great side, the problem side. And what I would say is, hey, we have a big problem. When you do import and export, there are regulations. And there are regulations in Japan we have a lot of rules sake in order just to sell sake to another country you have to fill out how many forms more than tens you have to fill out over ten forms just to sell sake to another country and in that country to import it to Korea how many forms on the other side you have to fill out we need to be that so what we're doing is we're taking this old process and we're going to use AI and our company Trade AI is going to make it incredibly fast and easy and reduce the error rate and take it from costing$50 ,000 in paperwork down to$50 in paperwork from 50 days of work to five hours of work.
50:45And we're going to do it across, we've identified 150 verticals in Japan and Sake is a declining one but the consumer electronics is a bigger one chips is an even bigger one we're going to take every form every antiquated and we're not putting it into the large language models we're putting it into an open source model that we control and this is something that chat gpt or claude or grok or gemini they won't even have these forms we're going to have these proprietary forms and by the way the forms change every 18 months on average now it's like whoa okay there's a big problem and ai is It's perfect for this problem.
51:23So you have the kernel of such a great idea and you have the passion for it. We just have to flip the entire presentation. We can fix it. Awesome. Thank you very much. Okay. Well done. Anything else you want to add, Thomas? No, it's great. Exactly that. Yeah. And especially for small business, right? I mean, God, that's like almost makes it, you go from being, I can't do this to, I have all these new markets. So it opens up the TAM for small businesses in a way that they didn't have before. Awesome. Hi, I'm Jason. Hi Tom, hi everyone. I'm founder of Homi World. Homi World is our social network.
51:56So here's the problem. Meeting the people in the real world, it became so hard, as you know. So to solve this problem, we built Homi. Here's a demo. So we, she's Maria, meet Maria. She just moved to Japan and she was head of an IT company. She was here only, she was looking for the event and the people and the event. So she feels who's coming. So she feels she is interesting because of the same interest and same occupations. So that is why she decided to join and chat to meet her. Not only that our AI understands her and recommends who to meet others and why, recommended by AI. So I want to connect her as well.
52:39So AI creates a personal message for both parties to attract each other. This is not just idea. This we have already launched. This already launched. So this is our business model. This is Omakase friend subscriptions. Our AI matches people every week if you pay. So these are attractions and so forth. So our core value is building an AI-native trust network on a map. That is why I believe we can expand other categories. Imagine the world, wherever you are, where you live, You have AI understand you very well and connect you the people and match you the events and stay places something like that.
53:22So this is our team. This is also our investors. One of them is like legendary consumer app founders before Facebook. And one of them is like a board and also co-founder of Pokemon Go. I have a last question before I leave. What can AI never replace in the 20 years, 30 years later? I believe real human connection in the real world. We empower real human connection in the real world. That's why we should exist for the world. Thank you very much. This is Homi. Thomas, we saw a very good-looking design. I love good design. What comes to mind? I'd want to know your background a little more. You kind of shot past that, but just obviously you've gotten some good people like the co-founder of Pokemon Go.
54:04You must have some pretty good industry experience. Definitely hit on that when you're doing the presentation. I know you don't have a lot of time, but what's your background? I have been managing a startup in Japan for seven years in the past. And that is like homestay matching platform. I know how trust network will happen, how people connect. So that's my background. Okay. I also do hosting more than 100 guest travelers in my home as well. That's perfect because it ties into what you're doing. It kind of demonstrates how you know about this space and why this is your idea. you know why you chose this idea because you you know a lot about it.
54:42COVID hit 19 hit I feel lonely at the time for two years traveling around the world but when I get most enjoyable experience I always meet the matchmakers to connect with people and something like that so when I back to home I host that hosting my guests at my home so they everyone looking for not place but people so I and when I introduce people or bar they feel like amazing so if you just say they if if you experience in the seamless way by the app or something that would be next level so I thought that was impossible because you know I thought of work and work and you know, not business model.
55:30But when I see that GPT launch, oh my God, that became possible. Because that is my story. Yeah, you know, consumer apps are incredibly hard until they're not. And it's very much about finding a behavioral loop that people become addicted to. And that actually solves that problem for them. And I'm not convinced that you've found it yet. But my friend started this company, Meetup.com. we talked about it the last time I was here, Scott Heiferman. And what they eventually found was that there were people who were weird, like you, who liked to be hosts, and like me, I like to host. And those people are called connectors, and they are really good at matchmaking and building people.
56:15How it grows beyond your ability to do it, and learning that loop that becomes viral, and you have this viral coefficient is going to be so critical. And it looks like you're figuring that out. And you just have to bring us along on that journey as investors. If it's for everybody to do anything, as investors, we're like, huh, what's the ICP? What's the beachhead market? Is it book clubs? Is it group dinners? Is it hiking? And you showed so many pictures, so many different things. I think it would be more effective to say, we know here in Japan, And there are three things that people are going to go crazy for.
56:55Everybody is looking for somebody to go on a day trip, get on a train and go to Kyoto or go on a hike. Everybody wants to be active and they're looking for somebody to play pickleball with or to go skiing with. So we're starting with those group activities. Ten people, going skiing, getting on the train. And then everybody loves to cook or explore restaurants. So we're doing a bar hop and going and eating street food. And here's the first one we did, and this grew into 20, and now it's 250, and here are the people who run those groups. I'm very interested in who are the Airbnb hosts of this? Who are the people who will build this, the eBay sellers?
57:36And that, to me, would be the magic, is if you know how to find the other weirdos. And people didn't, everybody thought eBay was like, people would just get rid of junk in their garage. They never anticipated that there would be people who would make it their full-time job. And that's something that now people can imagine because of Airbnb, because of being an Uber driver, because of, you know, all these weird monetizable hobbies, being a podcaster, being an influencer. So I'm very excited about your company. Your strength is design. And then go to market and explaining to us that the next piece for you will be that, I believe that'll get investors to this is for you to show us the growth journey and the top customers, the top verticals.
58:20The go-to market is, and you know, Zuckerberg had one. He's just like, I'm going to go after college campuses and dating and liking and just figuring out the relationship status. Now, if you were to look at the Meta Corporation now, it's not really about relationship status, is it? It's grown to be so many different things. And I'm trying to think of another example like snapchat it was really about people having these friendship streets for ephemeral messaging and making the messages disappear and it was like a private social network there's all these different devices of who the initial group is that builds the foundation my space was I think artistic people in LA who were trying to get you know was kind of pre influencer it was like the original influencers Paris Hilton had one it was like self-expression Self-expression and then maybe trying to even make yourself famous.
59:12Yeah, it was like that sort of combination. Here's a very interesting one. Is there somebody who makes a living doing this in your system now? Or do you know of somebody who makes a living hosting events like this? We're hosting by ourselves right now. So we don't yet have that. I wonder if hiking would be an interesting one. I saw hiking in there. What do you think is the most interesting two? For me personally or in the business? Which two do you think you could get to grow and double every month? I think we need to focus on the expat international and community and founder community in Japan.
59:46In Tokyo. Expat community. Expat community. Perfect. Yeah. That sounds like a great one. I would appreciate it. If you share the perspective, like how should we handle the focusing point in Tokyo or New York? Because if we focus too much on Tokyo, that will not become global standardized product. But your social network, I think we need to create some global standards. It's fine to start here. Yeah, and Tokyo is super in vogue, and it's also hard for foreigners to access Japan. You know, they don't speak the language. There are all these, like, secret spots. So I think you could take advantage of that.
1:00:16Also, I like that you really hit upon trust. You know, in order to meet someone in real life, I mean, especially for women, there has to be a trust component there. So I think that's definitely going to be part of your secret sauce is getting that right. I want to build on Thomas's comments there. Trusted. Right now, one of my theories of these kind of businesses and growth is I call it like hot embers. You know, like coal? I don't know that. Fire, small bits of fire. What do you call charcoal in Japanese? Sumi. Sumi. So if I have a brick of sumi and I put it here, it's hot. When we're sitting here, we don't feel it.
1:00:57That's one person. Then you put five people and you put them next to each other. Now we're going to feel a little bit of heat. Then you put 10 people on, you have 15 coals, they start heating everything up and we're going to step back. Whoa, it's getting hot. Then you put another 15 on. Whoa, it gets really hot. It's raining. It burns the desk. It burns to the floor. And you have to just very quickly build, or very slowly and methodically add that coal to the fire. And I think that would be very interesting for expats. So if there is a German, Germans in Japan, and Americans in Japan, and French people in Japan, that's really fascinating.
1:01:33Because then when I come here, I started a group with the people we had lunch with that time. And I was like, hey, I'm thinking about going skiing. Hey, I'm looking for a place to stay. Hey, I'm looking for this. And I popped up my own little one. And people started giving me good advice. And then people started giving me direct advice. Hey, this hotel is like a secret one. I didn't want to put it in the group chat. But it's really like a little bit less expensive. And here's the person. man if you can solve problems for people like that that feels like a great place to start and you want to start in your own backyard with something you know and you can be successful at and that you're going to enjoy doing expat sounds perfect thank you very much because there's expat bars here in Roppongi somebody took me to one I think it might have been champagne only but all the Americans were going to this one place in Roppongi that was a champagne bar it's very weird but there's a is there American expat are there American expat places here that America yeah yeah is it is it like a specific neighborhood or is it just specific spots well punky but lots lots of spots lots of spots where if you go there you see the Americans is there equivalent for Germans and French yeah yeah that's and where does that exist how would I find that read it maybe there's a subreddit or something how would I ever be aware of it some yep learn from a friend right well especially if someone can take you you and then bring you around I think is and this you know if you trust you met someone on this app and then you can trust that they're not gonna you know that they're like a nice person it figures out mutual contacts or whatever imagine the experience where you're whenever you come to find like place here not only find stay so you can seamlessly group spontaneously group to welcome you like this is the handle by AI so that you know I think I believe but we can change the way to how do we connect people.
1:03:14So that's my strong conviction about how we change the people connect. All right, big round of applause for our presenters and for Thomas.
From the publisher
This Week In Startups is made possible by:
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Today’s show:
Some pitches sound just like ads… and it’s a huge red flag for investors.
On our latest edition of TWiST Tokyo, Jason welcomes legendary angel investor (and long-time friend of the pod) Thomas McInerney. His list of investments reads like a Who’s Who of the tech elite, including Notion, SpaceX, Uber, OpenAI, Anthropic, and Perplexity….
At Founder University x Tokyo, they discuss how the angel investing landscape has shifted, why it’s so important for founders to stay humble, the reasons that investors need to stay not just optimistic but aggressively so, and what angels can add to companies beyond just writing checks.
Plus we revisit some classic TWiST clips featuring Thomas from over 10 years ago AND take a look at three of our favorite pitches from our Japanese founders.
Timestamps:
(00:00) FLASHBACK: Clips from Tom’s classic TWiST appearances
(02:54) Why Jason and Tom love hanging and building in Tokyo.
(05:30) How has the angel investing landscape changed over the last decade plus?
(09:38) “Being an investor is a commodity… You have to provide more than just money.”
(12:17) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist
(13:34) How Thomas evaluates very early stage startups
(14:56) Why Thomas invested in nuclear tech when it was hugely unpopular
(17:31) Why it’s so important for new founders to be both humble and smart
(18:50) The relevance and accuracy of Marc Andreessen’s “Idea Maze” metaphor
(20:40) Deel - Founders ship faster on Deel. Set up payroll for any country in minutes and get back to building. Visit http://deel.com/twist to learn more.
(21:41) How Elon Musk brings oversized, visionary ideas to life
(26:11) Why founders using buzzwords is a huge red flag
(27:13) The little “poker tells” Thomas and Jason look for in a founder
(28:26) “If there’s any doubt, there’s no doubt.”
(30:47) LinkedIn Jobs - post your job for free at http://linkedIn.com/twist then promote it to get access to LinkedIn Jobs’ new AI assistant.
(32:04) PRO TIP: Don’t run out of money!
(38:10) The importance of being an aggressive optimist for investors
(43:27) The human brain cannot comprehend 1000x growth
(45:33) PITCH #1: Sakenomist is the cross-border commerce platform, starting with sake exporters (Hiroshi Takeuchi)
(51:47) PITCH #2: HomiiWorld, the IRL social app which helps you meet new people anywhere in the world
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Thank you to our partners:
(12:17) Lemon.io - Get 15% off your first 4 weeks of developer time at https://lemon.io/twist
(20:40) Deel - Founders ship faster on Deel. Set up payroll for any country in minutes and get back to building. Visit http://deel.com/twist to learn more.
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Great TWIST interviews:
Will Guidara
https://youtu.be/pvJa2pzuXWQ
Eoghan McCabe
https://youtu.be/9dHN4YFkgv4
Steve Huffman
https://podcasts.apple.com/us/podcast/reddit-ceo-steve-huffman-on-mod-revolt-building-a/id315114957?i=1000617333424
Brian Chesky
https://podcasts.apple.com/ca/podcast/airbnb-ceo-brian-chesky-on-early-rejection-customer/id315114957?i=1000611761112
Bob Moesta
https://youtu.be/y2UMzSqX94Q




