Where early-stage founders must focus to succeed | E2244

Summary

Recorded from Tokyo during Founder University’s international expansion, Jason Calacanis is joined by Amanda Bradford (founder of The League, sold to Match.com) and William Barnes (formerly of Uber) for a tactical masterclass aimed at “Year Zero” founders. The trio emphasizes a “product-first, fundraising-second” mentality, arguing that modern tools like AI and vibe coding allow founders to validate MVPs and achieve product-market fit before seeking external capital. A central theme is customer obsession: the guests urge founders to stay lean, solve specific pain points, and avoid the “feature death march” by maintaining essentialist focus on reliability and trust.

The conversation delves into tactical execution of growth and team building. The panel highlights the importance of constraints — limited geographic launches or tight deadlines — as catalysts for innovation. Distribution is framed as a founder’s primary job, requiring creative PR hacks and advocate-building rather than large marketing budgets. For hiring, they recommend seeking “high-slope” generalists with high grit and low neuroticism who can thrive in chaos. The episode concludes with a philosophical reflection on success, noting that while wealth serves as an amplifier for vision, the true reward of entrepreneurship remains the intellectual challenge of building something meaningful.

This Tokyo edition captures the energy of an international founder community and provides a dense collection of actionable startup advice distilled from years of building and investing experience.

Highlights

”Focus is everything in the early stages”

“Focus is everything in the early stages.” — Amanda Bradford, 11:43

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”You can make a clickable prototype in Figma”

“Yeah like with my company we would even go before I even had a prototype built while that was being developed I basically strung together screenshots that you know you’d use in Figma and you can make a clickable prototype.” — Amanda Bradford, 6:36

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”Distribution — we’re cooking with oil right now”

“Next up we want to talk about distribution, we’re cooking with oil right now. First up we talked about product first, let’s put the fundraising down the road.” — Jason Calacanis, 36:00

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”Focus heavily on generalists that have incredible attitudes and like high slope”

“Yeah, then I would focus heavily on generalists that have incredible attitudes and like high slope.” — William Barnes, 49:33

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”Great art is driven by constraint”

“Let’s talk about constraint. There’s this expression that great art is driven by constraint.” — Jason Calacanis, 28:14

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Key Points

• Tokyo Founder University (0:00) - International expansion of founder education program, recording from Japan
• Amanda Bradford’s exit (2:08) - Sold The League to Match.com, now “resting investing”
• Cash flow management before PMF (3:19) - Preserve cash and stay lean until you find product-market fit
• First-time founder mistakes (5:57) - Getting the order of operations wrong: build before you fundraise
• Build something, even if taped together (6:45) - MVP validation matters more than polish
• Focus is everything (11:19) - Obsessive focus on one thing before expanding
• From a wedge to a bridge (14:17) - Start narrow and expand from a dominant position
• The “Not Right Now” list (18:45) - Explicitly writing down what you will NOT do to maintain focus
• Embracing simplicity (19:11) - Simpler products are more reliable and trustworthy
• Trust and reliability for Uber (22:00) - William Barnes on how trust was everything for Uber’s early growth
• Constraints as catalysts (28:12) - Limited resources force creative solutions
• Overdeliver for word of mouth (33:40) - Exceeding expectations drives organic growth
• Distribution as founder’s primary job (36:32) - Most founders underinvest in distribution
• Favorite distribution hacks (38:19) - Creative PR, influencer outreach, turning power users into advocates
• Japan’s commitment to excellence (45:54) - Jason’s respect for Japanese culture of competency
• High-slope hiring (49:38) - Prioritize fast learners with grit over experienced but low-energy candidates
• Team transitions (53:11) - Moving from early-stage chaos team to growth-stage specialists
• Whoever writes it down gets credit (57:45) - Documentation discipline for ideas and decisions
• Has the meaning of money changed? (58:04) - Philosophical reflection on wealth after successful exits

Mentions

Companies

• The League (2:08) - Amanda Bradford’s dating app, sold to Match.com
• Match.com (2:08) - Acquired The League
• Uber (22:00) - William Barnes’s former employer, used as case study for trust/reliability
• Founder University (0:00) - Jason’s founder education program, now expanding to Japan
• Quadratic (15:50) - AI spreadsheet tool, show sponsor

People

• Amanda Bradford (2:07) - Founder of The League, sold to Match.com
• William P. Barnes (2:49) - Formerly of Uber, startup advisor

Surprising Quotes

“Money has non-linear value. Each incremental dollar you get becomes worth less than the one you had before… It’s an amplifier. I think people need money obviously, but once you hit a certain threshold, acquiring more money is not about the utility it provides, it’s about kind of the psychology of it.” — William Barnes, 58:24

“Because it’s not… I don’t think you can just do a good job. You have to absolutely nail it and like over-deliver if you want to drive word of mouth.” — William Barnes, 33:39

“And then he would tell the internal team, ‘It’s on the not right now list.’” — Jason Calacanis, 19:06

“Let’s talk about constraint. There’s this expression that great art is driven by constraint.” — Jason Calacanis, 28:14

Transcript

Jason Calacanis: 0:00 All right, everybody, welcome back to This Week in Startups. I’m your host, Jason Calacanis. I am still in Japan and loving it. We’ve had an amazing time here launching Founder University. What’s Founder University? If you haven’t been listening to the program in the past year, where have you been, number one? Number two, it’s a 12-week program that we started in the United States to help founders who are in year zero. In other words, they might not even be incorporated, they might still be building their team or finding a co-founder. They’re in that year zero. They know they’re going to start, they’re not sure when. And as part of that program in the United States, we look for companies that we might want to invest in. And then they go on to our accelerator or some of them go on to Y Combinator, Techstars, Antler, all these great programs all around the world, 500 Global. So it’s a pre-accelerator. We launched it in the fall in the Middle East, specifically in Riyadh, in Saudi, with our partner, Sunabel, which is the venture arm of the PIF there, the sovereign wealth fund. And now we’ve launched it again here in Japan with the greatest partner you could ever have, JETRO, which is essentially the economic trade group here in Japan that is supporting founders. And Japan is going through such an amazing, amazing resurgence. Not that it ever went away, but young people in Japan are looking at startups again as a viable career path. And in a country where they have very low unemployment and plenty of jobs available, it’s a very interesting moment in time when people will give up the security of those jobs to take the risk of starting a company. And that’s what we do at our fund. So today we’re going to talk about what should founders in year zero, the year, you know, right as they’re starting to incorporate, maybe even launch their product, what should they focus on? I’m very lucky to have two great friends in Austin. Amanda Bradford founded The League. We met Amanda, I think, at the Sequoia Scouts program. And you’ve been on a bit of sabbatical, your non-compete or…

Amanda Bradford: 2:07 Resting investing.

Jason Calacanis: 2:08 Resting investing after selling your company to Match.com?

Amanda Bradford: 2:13 Yes.

Jason Calacanis: 2:13 Congratulations on that. So you’ve taken a company from the cradle all the way to the grave, all the way to sell.

Amanda Bradford: 2:19 Hopefully not the grave, but…

Jason Calacanis: 2:21 Not the grave, but I think you get the idea.

Amanda Bradford: 2:23 To bigger and better things.

Jason Calacanis: 2:25 Yes, to bigger and better things. You did a great talk here for the founders in this program, and you also came with me to Saudi. And so we’ll talk today about what people should focus on. Pretty open dialogue, of course. One of my besties, William Barnes, is here. He was Travis’s right-hand man, left-hand man, front, back, everything. You got to work with Travis in the boom years of Uber.

William Barnes: 2:49 Yes.

Jason Calacanis: 2:50 Also got to come with me to Saudi.

William Barnes: 2:52 Yep.

Jason Calacanis: 2:53 And here. So let me start with that. You know, we’ve now launched the program in just five months or so in two cities. What have each of you noted about each of those cities and what founders in year zero… …are most often asking you about as mentors in our program.

William Barnes: 3:04 Well, I think the experience in Saudi and here is the entrepreneurial spirit is invigorating and kind of reminds me of being back in San Francisco, you know, 10, 15 years ago. There’s so much kind of opportunity, and that’s, that’s very exciting. And the other thing that I’ve seen through the, you know, the investing with my Bunch fund and also speaking to founders here is I think one of the things that we’ve seen a lot is cash flow management. It’s so easy to run out of money.

Jason Calacanis: 3:32 Yes.

William Barnes: 3:33 And I think keeping a focus on keeping the burn low before they find product market fit I think is a is a key thing. I think a lot of people get excited, they see all the headlines about, you know, Facebook or you know, maybe one of their friends raises a series B or a C and I think they get out ahead of themselves trying to build a company before they’ve found a product. And so trying to spend as little money as possible to find some product to scale.

Jason Calacanis: 3:57 Yeah, and we’ll unpack that in just a moment. Amanda, what have you noticed in meeting the founders in Saudi, in Riyadh, and here in Tokyo, Japan?

Amanda Bradford: 4:03 Well, there’s tons of opportunity. I think everyone’s been… the breadth of startups I’ve been very impressed with, everything from healthcare to defense tech to consumer marketplaces. So I’ve been just impressed with the scope of of what everyone’s trying to tackle. I think the questions I’ve been getting the most at least me as someone who’s built zero to one is is around hiring, is around finding co-founders, when should someone be a co-founder, when should you outsource, when should you fundraise, at what point in your kind of product development process should you go and ask for capital from investors? And similar to kind of Will’s point and I always recommend people get an MVP or a minimum viable product up and running and show investors that this product is going to be built regardless of if you take money from them and show them that, you know, this this train is is leaving the station and kind of put a little bit of skin in the game yourself, whether it’s using some of your own money or getting people to work for equity, but but really kind of showing a little bit of traction prior to going out and asking for money. I think that’s a big…

Jason Calacanis: 5:02 Okay. So I think we’re going to start with what has come up now over and over again, which is product market fit first, product first, fundraising second. I think it’s a a fine way to put it, yeah, Will?

William Barnes: 5:18 I think there’s you’ve got to stage it and it depends on your life situation whether or not you’re you have a lot of the time, you know, whether you’ve got some savings, but I think there’s a lot that you can do before you start spending a lot of money or certainly before you raise money. And I think Amanda, you know, talked about that on her presentation yesterday. You can go meet customers, you can kind of understand the problems they’re facing and you can especially in today’s environment, whether it’s vibe coding or having a very hacky front end and then doing things manually to try to validate whether or not you’re solving a real problem. And I think evenings, weekends and using some of the AI tools, you can get a lot done to get some signal that what you’re building is valuable or useful to somebody. And you can do all of those things before you raise money.

Jason Calacanis: 5:57 And I want to unpack what you said before, which is Founders maybe especially first-time ones have this order of operations wrong. They think they need to convince investors of their vision and land some giant amount of money and then deploy capital. Why is that wrong in 2026 as we sit here today?

William Barnes: 6:19 Well I mean I think you know you’ve been in the industry for a good amount of time I think you know a long time ago you would have to raise a lot of money and then build all this infrastructure whether it’s like servers, HR people, legal you’d do all of those things to try and get a product out there in the hands of a customer and I think you know through a whole range of technology you can now do a lot of that validation without needing a lot of money and I think that’s why it’s kind of moved how people should approach creating an MVP.

Amanda Bradford: 6:36 Yeah like with my company we would even go before I even had a prototype built while that was being developed I basically strung together screenshots that you know you’d use in Figma and you can make it so that you know you click on a button and it opens another screen so if you’re showing it to a customer it feels like the app is built like my mom thought the app was built but it was really just a series of like eight screenshots hyperlinked to each other so you can kind of do these hacky things to just initially get some do a temperature check with people to say hey would this be interesting to you.

Jason Calacanis: 7:15 And that was 10 years ago.

Amanda Bradford: 7:17 Yeah.

Jason Calacanis: 7:18 And now you can basically vibe code these now in a weekend.

William Barnes: 7:22 And you learn a lot through doing that you’re going to get like feedback yes no people aren’t going to sign up or they are going to sign up and you learn things about your messaging.

Amanda Bradford: 7:28 And we tested our onboarding for almost five months because that’s how long it took me to develop my app and what we learned an example for us was we you know I had had LinkedIn I was asking people to submit their LinkedIn to be able to apply to the league because we were that was how we used to to kind of vet our applicants but people got very weirded out by having LinkedIn be the first thing no one was used to that they wanted to they were fine connecting Facebook but LinkedIn freaked them out so I basically because of the focus groups I did I changed the order and I put Facebook connect first and then by that time the users sort of already invested in the onboarding flow and then by putting the LinkedIn second we had a much higher completion rate than just by putting LinkedIn first.

Jason Calacanis: 8:00 And that didn’t require you to get permission from a seed fund with a 250K check that required you to be thoughtful and to talk to customers and to run these little experiments and that scientific method talked about in the Lean Startup or the Startup Engine lots of different people have…

Amanda Bradford: 8:11 My scientific method was taking women to a wine night and asking you know give me feedback on this onboarding but yes it was it was scientific in some respects.

Jason Calacanis: 8:17 And those were clickable mockups and now we have vibe coding.

Amanda Bradford: 8:20 Yep.

Jason Calacanis: 8:21 So very important.

Amanda Bradford: 8:22 It’s a very exciting time to build right now I will say.

Jason Calacanis: 8:24 Yes, in Year 0 you can actually build these prototypes and test them they don’t have to be just clickable mockups. So let’s go to our what I think is our second point I think we’ve pretty much have consensus of this I’m going to put it as second but we will order these as we go. Finding those first customers doing customer research having met with the companies now and heard some stories about how they’re doing that and our own personal experience doing it what are the… …best practices front of mind for you right now, William Barnes?

William Barnes: 9:04 Well, I think this is why the cliché is still true, which is find a niche and try and go really kind of narrow. There’s a variety of benefits to picking a narrow niche. You can tailor your messaging and the MVP to that niche so the customer profile that you’re talking to, they’re going to feel more special for want of a better word, and the marketing and the MVP is going to be more tailored to the problem that you’re trying to solve for them. There’s a higher chance that they’re going to engage with you because they’re going to feel like it’s a specific solution to their problem. So the niching down I think is incredibly helpful and you’ll learn more quickly. You know, if you go and talk to, you know, 15 back offices that do importing and exporting in Japan, you’re going to learn more quickly because you’re having a similar conversation with a similar customer profile. So there’s kind of like two benefits there of picking that niche.

Jason Calacanis: 9:56 So you picked that niche, we had an interesting company yesterday that pitched. In this one example, importing of exporting of products is a lot of paperwork. And you and I were talking about it at breakfast today, what a great idea it was. The pitch was a little bit off, the order of operations might have been wrong, but we both thought, “Wow, it’s so messy in that back office.” And if you talk to 15 of them, you say, “It’s just for the back office operations of an export company, what actually happens in that pit? What happens in that boiler room, that back room where it’s occurring?” And how much progress can you make? Now, you might find out that there’s not that much to it and you’re going to very quickly solve their problems, but then you will inevitably discover more.

William Barnes: 10:41 Yeah, you’ll discover… You know, I think one of the reflections you and I had is they were kind of bundling two businesses together. There’s the consumer facing part and then it was almost they were going to figure out the import-export paperwork to serve the consumer facing. And I think what you and I talked about is maybe unbundle those two things and focus just on the kind of the workflow piece and then go and speak to, you know, a narrow set of customers, you know, all in, you know, the consumer facing product piece, but just go and solve that one and then make that a business first, and it’s more narrow niche.

Jason Calacanis: 11:11 And dove-tailing that, Amanda, with the first point we made, which is, “Hey, get that product really tight and the fundraising will come later.” If you’re going to raise money and you’ve got two different products and they’re extremely different, you’re now scaring an investor or an angel that, “Oh my God, you’re building a consumer business and an enterprise business at the same time? Oh, and then you’re explaining the marketplace?” We’ve never seen that. Like, Airbnb does not have an enterprise business.

William Barnes: 11:42 Still.

Amanda Bradford: 11:43 Focus is everything in the early stages.

Jason Calacanis: 11:45 Exactly. And if you want to… and we’ll get to Frigalia later, but that customer obsession seems super critical. You specialize in that. I think maybe that is your superpower is this customer obsession when we saw pitches yesterday and you’ve talked to companies here in Tokyo… at Waseda University in Japan. What’s top of mind for you thinking about maybe your next startup and customer, don’t tell anybody what it is, but just customer obsession and how you will go into your next startup with this new inspiration having met so many of these companies in Saudi and here in Tokyo. What’s- what’s top of mind for you in customer startup?

Amanda Bradford: 12:21 Well I think it’s, yeah, it’s super serving a niche audience and I think Peter Thiel talks about this a lot with, you know, PayPal it was the early eBay power users, and with Amazon it was a bookstore. And, you know, eBay initially, eBay was Pez dispensers, right? So it’s- it may be a market that people immediately might say that’s a small TAM, that’s not big enough. But if you can like win that market, then there’s going to be concentric markets that you can then go after. So- so don’t be afraid to go super niche. With us, you know, I was going after sort of like women who are like 28 to 34 who are career-oriented, who were struggling with the dating- current dating apps and how dating worked. And so we, you know, people called my app MBA Date at the beginning because there were so many MBAs on it and that was the demo that I- I knew really well as an MBA and I said, I am going to make sure it works for this very small audience. And then of course they told friends, other people, you know, we eventually were more than just a 28 to 34-year-old demographic, but we started very niche and I had a lot of investors be like, your TAM’s not big enough. So kind of don’t be scared of a small market to start.

Jason Calacanis: 13:25 Well, let’s talk about that. TAM not big enough. There is a very simple way to address that when talking to investors. And remember, you’re building your business, you’re not building a performance to give to a venture capitalist that gets them to unlock money. Like, you may have to do some things that are performative and answer questions, of course, but at its core, you need to have some niche audience that’s willing to embrace your product. 28 to 34-year-old women who have MBAs who, you know, are desirable in market and are going to approach maybe dating differently than an- you know, average person, it’s a really interesting group to start with. You know in your heart of hearts, if it works for this group, there’s adjacencies, there’s adjacencies, there’s a next group. If it works for, you know, the back office in Japan, it might work for the back office in India. It might be slightly different, but they’re still doing the same function, which is exporting something.

William Barnes: 14:18 What’s worked well with me when I get pitched this by founders is a framing around sequencing, right? So it’s like I win this small piece of the market and then…

Amanda Bradford: 14:30 It’s a wedge, right?

William Barnes: 14:31 It’s a wedge, and then I can sequence this to a bridge to a slightly bigger market. And then when I really like it when founders say, well, here’s the trigger for when we move to the next part.

Jason Calacanis: 14:40 Oh, so they’re actually detailing the journey first and like what milestones need to be hit.

William Barnes: 14:45 Yes. Yeah, we’re going to get to the new world, then…

Amanda Bradford: 14:51 Land and expand. Land and expand.

William Barnes: 14:56 Land and expand. So now here we are, we’re in the Northeast, but we’re going to go figure out where are the different things we can find. There might be good… And they kind of handhold me through this sequence of small, medium and then like there’s this huge market that we’re going to earn the right to. But we’re laser-focused on…

Jason Calacanis: 15:00 Which makes you more credible.

William Barnes: 15:00 Yeah, 100%.

Jason Calacanis: 15:01 And that’s I think maybe where some founders get tripped up. They think, oh, I’m going to do this and I’ll be less credible.

William Barnes: 15:09 No, you can sequence it as you’re saying.

Jason Calacanis: 15:10 When we win this war and we get the beach, then we’ll go to the, you know, a little bit further in land. We’ll secure the beach first. We get that beachhead market. That’s why that term exists. It’s a military term, secure the the beachhead. Okay, when we get back from a quick commercial break, I want to talk about founders going on the feature death march. Founders putting their head down and spending too much time building 10 or 20 features as opposed to the essentialism of finding what is the core feature loop value of my product. When we get back on this week in startups. If you want to be a data-driven founder, and trust me, you do, you’re going to need to spend some time in spreadsheets building models and doing projections, but so many of these spreadsheet programs are stuck in the 90s. Thankfully, now there’s Quadratic, finally bringing the productivity boost of AI into your spreadsheets. But this isn’t like some simple chatbot in the corner who can answer your questions. No. This is an AI native platform that handles all the number crunching and organization for you. You just describe what you want to do with your data and Quadratic makes it happen right there in the spreadsheet. Now, you can get insights about your business without fighting formulas, and you can immediately share your results with your team and all of your collaborators. No setup or payments are required upfront. You can just start using Quadratic right now. It’s going to blow your mind. Visit quadratic.ai/twist to sign up. And use the code twist to get a free month of their pro tier subscription. That’s Q-U-A-D-R-A-T-I-C.ai/twist, quadratic.ai/twist. All right, we’re back at This Week in Startups here. We’re working down our list of things that founders should focus on in year zero. Building the team, finding the customers. This is before you raise money when you’re kind of doing that product discovery and figuring out what your startup will be. Amanda Bradford’s with me. She built The League and sold it to match.com and she’s going to do another startup at some point. She angel invests. William Barnes from Carman Ventures. Let’s talk about founders going on that feature death march. They can’t help themselves. They love building features. They get a little too precious, don’t they, William?

Amanda Bradford: 17:36 And customers also love giving feature requests.

William Barnes: 17:39 Yes, they do.

Jason Calacanis: 17:40 Oh, yeah. I mean, this is like the two things that will make founders go off track.

William Barnes: 17:44 Yeah, 100%. I think it’s an expression of psychology and I think there’s kind of there’s two parts to it. There’s a fear of going talking to more customers or doing more sales. It’s like a fear of that. Like I don’t want to go and do more sales and get more rejection. So here’s something I can control and like I can go and ship more product. Yeah. And the other one is it’s an avoidance of not having product-market fit and finding one feature that really solves a pain point and the customers using a lot. There are some exceptions to the rule like if you’re, you know, you’re trying to build a complex enterprise product or like, you know, a horizontal piece of software. You are going to need to be more feature-rich. But I think in general, having the discipline to find one or two features that really solve something painful and then charging for it and then doing a lot of sales around it is the prevailing wisdom.

Jason Calacanis: 18:32 And if you do it that way, there’s an essentialism. You understand and you’ve prioritized the feature set. It doesn’t mean that you’re not going to add those features later.

William Barnes: 18:44 Yeah. Sequencing again.

Jason Calacanis: 18:46 Sequencing again. And I had a founder who said the way he handled it inside his startup was he made, he said he would say to the team members or investors or customers: ‘It’s a great idea. I’m going to write it down so we don’t forget it here and we’re going to put it in a, we’re going to prioritize it and we’re going to do a little research on it.’ And then he would tell the internal team, ‘It’s on the not right now list.’

Amanda Bradford: 19:08 The backlog, yep.

Jason Calacanis: 19:09 The backlog, yep. But ‘not right now’ was a very kind way of saying it to the team and it showed leadership. And let’s talk a little bit about the simplicity of some of the most successful products in the world. Instagram, Amanda had the most simple…

Amanda Bradford: 19:25 Just sending postcards to each other.

Jason Calacanis: 19:27 Essentially. The, you upload a photo to the social feed, that’s one function, and then you pick a filter by swiping and hit publish. That was it. They didn’t even have a like button in the beginning. They certainly didn’t have comments. And then those were added later. And if you open Instagram now, I feel like I am launching a rocket ship. I mean, there are so many features when you swipe left. Am I doing a story? Am I doing a post? A reel? I mean, I don’t know the difference between any of these things and then there’s a bunch of buttons and you can do filters and there’s thousands of lenses you can put music behind it. It’s so convoluted but still growing. When you start thinking about your first product at The League, what was the analogy there?

Amanda Bradford: 20:11 Oh, it was, it was simple AF, I would call it. Basically it was five at five: you get five daily prospects at 5 p.m. and that was it. You could message them, nothing else. We didn’t even monetize for about two years. So especially in consumer, I always say make sure you’re actually building something that people want before you start charging them. And so we did kind of a smoke-and-mirrors implementation where I wanted to be able to tell my investors that I do have people willing to pay, you know, we were servicing a high-net-worth demographic. So I actually created a fake button where users could say ‘I want to upgrade.’ We knew that about 10 to 15 percent of people would click that button and then we actually gave them the feature but we didn’t actually charge their card because I wanted to be very simple and very focused on just let’s make the basic free product amazing and know that we had a 10 to 15 percent conversion rate but not actually get distracted by payments yet. dealing with monetization with billing with with refunds which happens in consumer and so that’s like an example of kind of how you can sort of hack your way into building a little bit of features so you know there’s a demand without without ruining your focus.

Jason Calacanis: 21:12 But so elegantly simple yet complex. Five matches. 5:00 p.m.

Amanda Bradford: 21:16 Smoke and mirrors. Yeah.

Jason Calacanis: 21:17 I mean you say smoke and mirrors, I say essentialism. It gives you exactly what you’re looking for. 15 would be overwhelming. Now it’s a chore. Five? Sounds like it takes five minutes.

Amanda Bradford: 21:27 Yep. And our thing was quality over quantity, right? So that was our main message. That’s how we differentiated from Tinder from all these other apps out there was just you’re going to get five good prospects a day at 5:00 p.m.

Jason Calacanis: 21:37 Which we’ll get into a minute in in our discussion about trust but let’s keep talking about like the feature essentialism and avoiding the feature death march. What was it at Uber? I mean I have my own ideas but you were inside that.

William Barnes: 21:47 I mean obviously with a high frequency consumer product you are inundated all week with people making feature requests or suggestions. And as the team got bigger, you know people were constantly making suggestions to Travis. I mean Travis was relentless about focusing on reliability. As you can imagine if you take Uber to travel from your office or your home to somewhere other in the city and you take it there on a Friday or Saturday night and then it gets to the end of the evening and you want to go home and it doesn’t work, you’re not going to use Uber again. And this is in a world and in many cities unlike Tokyo where the taxis are not reliable so you can quite literally be stranded. Um and so we focused a lot in the early days on making it reliable. And to I think to say yes to reliability we had to say no to a lot of other things because for that reliability took a lot of operational and engineering resources. And so we we were pretty obsessive about completed request, ETA which was just like the time it would take to complete a request, and the driver rating. And we knew we had a product that had product market fit so we were just very very focused on making the thing that already had product market fit work really really well.

Jason Calacanis: 22:59 So our first item, hey, let’s get that product right first and we’ll worry about fundraising down the road. Which means you have to be our second point, customer obsessed really understand the customers which costs zero dollars. That’s one of the beautiful things and then today with Vibe Coded, even doing product first and these little experiments, also zero dollars. Three, we want to avoid that death march with features. You really want to focus on what’s essential. Now we’re going to open up our fourth point today of what founders should focus on in year zero which you did a perfect transition to which is trust. Relentless focus on trust and reliability. Trust and reliability. Amanda in dating this is incredibly important as well.

Amanda Bradford: 23:45 Trust is everything.

Jason Calacanis: 23:46 Yeah. So so tell us about that and how much it cost to do that the right way, the resources it took and and how you think about it sitting here today looking back on that decade long journey to a very successful exit and then carrying that into whatever your next product will wind up being. I know you’re choosing between three or four ideas. One of which you got inspired by here on the trip, but we won’t—

Amanda Bradford: 24:03 A lot of ideas. A lot of domains in my GoDaddy shopping cart right now. Yeah, so for us trust was, you know, can you trust that this product is going to serve you prospects or dating candidates, should you say, that you want, that you know, fit your preferences? And for us, I actually vetted every single applicant manually. So, you know, eventually we did transition to using algorithms and machine learning and all that fancy stuff, but at the beginning it was literally me, Amanda, looking at everyone who applied and saying, ‘You’re accepted,’ and ‘You’re rejected.’ And people downloaded The League and joined The League because of that, you know, reliability or trust that the people are going to be high quality, vetted. They’re going to have six photos. They’re not going to do gym selfies. They’re not going to be wearing sunglasses in their pictures or they would be rejected.

Jason Calacanis: 24:46 And those were specific things you did. No gym clothes, no—

Amanda Bradford: 24:50 Oh yeah, we had a whole rules of… eventually I trained people to do this. I wasn’t always the one accepting all the candidates, but eventually, you know, we found we had almost a 50% acceptance rate as far as when people get a prospect—we call them prospects—in their batch, 50% of the time they liked them, which, you know, if you’ve been on any dating app today, you know, usually it’s probably like one out of 20 that you’re going to be swiping right on. And so getting a 50% acceptance rate was sort of unheard of and is still unheard of today. And so that was because we spent, you know, a lot of… we did a lot of things that didn’t scale. That was what I was doing didn’t scale. And then we also did customer support, so I had a human—that was me at the beginning too—the concierge. We had a concierge that would answer every question from a user regardless of if they paid us or not. Help them with their profile. We said, ‘Hey, your third photo is actually better than your first. I went ahead and swapped it for you.’ And I would actually go… I remember before we launched, guys in particular are very bad at curating their photos. So I would go and take, find the best photo of the six they put and put it first. And then I turned everybody’s photo black and white because everyone looks better in black and white. So we did a lot of these things that just made things, you know, made people trust the product and want to come back.

Jason Calacanis: 25:54 In the case of Airbnb, they said the photos were critical and there’s this famous story that the founders always tell of, you know, talking to Paul Graham at YC about—

William Barnes: 26:07 Getting the professional photo shoots, right?

Jason Calacanis: 26:10 Getting the professional photos and he said, ‘Well, and then…’ and he said, ‘Hey, the most demand’s in New York.’ He says, ‘So why aren’t you in New York with cameras taking pictures of the best places and hiring photographers?’ And they were like, ‘Oh, because we’re startup founders and we want to focus on anything that’s not the most essential thing.’ And that’s what great mentors, great investors, or great programs like YC or hopefully ours can help you do, which is get to that essential important thing.

William Barnes: 26:30 Yep. And those photos build trust. If you’re going to stay somewhere and the photos look like a serial killer’s apartment, you’re not going to book it. But if it looks like the Aman hotel or it looks like the Ritz Carlton, okay, yeah, maybe I will stay there.

Jason Calacanis: 26:53 Which is why, William, when you look, they almost have a playbook of what the kitchen should look like, and they have a neon sign, and then they have the pods, the coffee… I mean, they’ve literally figured out, when you hear— For Amanda to talk about it, it seems obvious, but each of those nuances builds trust.

William Barnes: 27:05 What I hear when Amanda tells that story is somebody that is obsessed about making the core value proposition reliable. I mean, she’s obsessively vetting everybody, she’s committed to five matches a day, or like five offerings a day, and she’s handholding the, you know, kind of what she’s serving up and she’s saying no to all these other features. And I think that level of obsession and, you know, not using tech necessarily and doing something that doesn’t scale is a way to do that.

Jason Calacanis: 27:40 Okay, we’ve gone through four really important things that founders should focus on in year zero. We’ve got three to go. First up, hey, let’s get focused on that product, don’t worry about fundraising. Number two, customer obsession. Number three, feature death march, feature creep, just staying really focused on making the thing the thing. And of course fourth, working on that reliability and trust in your product. These are really important things to think about right now in year zero. And if you’re listening to this and you’re thinking about starting a company, you can go to founder.university, apply for the US, Riyadh, or coming to Tokyo, and everybody can apply to all three. It’s competitive to get in. Let’s talk about constraint. There’s this expression that great art is driven by constraint.

William Barnes: 28:16 Yeah, innovation needs a constraining variable.

Jason Calacanis: 28:17 Yeah. And they asked Bob Dylan, one of my favorite artists of all time, my favorite album happens to be Blood on the Tracks. And they said in this Rolling Stone interview, ‘My gosh, this is my favorite album,’ and it starts to talk about all these incredible songs and ‘What was the inspiration for this album?’ And Bob Dylan said, ‘Well, you know, I owed Columbia Records a picture, I owed them an album, and they’d been waiting a long time, and they said if I didn’t get it to them by this date, they would sue me to get the advance back. And I didn’t have any money, I’d just been through a divorce.’

William Barnes: 28:57 Yeah.

Jason Calacanis: 28:58 And this poor interviewer was crushed that this album that meant so much to them, and I rated it, I was crushed, that the inspiration of the album was the divorce and not getting sued because he was broke. That was the inspiration. There was a limiting factor. When you’re making a movie, you have a certain number of days to shoot. With a startup, you have…

William Barnes: 29:12 You can drag it out if you want, but you have the gun against your head of your burn rate, like how much money you have left.

Jason Calacanis: 29:25 Right.

William Barnes: 29:26 And I think cash flow management is the most important thing when it comes to managing a startup. Like running out of money means the game’s over. One thing I’ve seen time and time again, I get hundreds of investor updates, is you have some founders that I think get attracted to company building. You know, they want to play company building rather than finding a product that works and then testing and improving that they can scale it in a economically rational way where the unit economics… economics makes sense. You know, I think David Sacks came up with this term of burn multiple. Like how much, for every dollar that you spend, what’s the incremental revenue that you generate?

Jason Calacanis: 30:08 Right. There’s constraint.

William Barnes: 30:10 Yeah, there’s a constraint, right? And I think for, I’d defer to David on this one, but I think for a lot of, you know, SaaS metrics, you know, under two is, you know, a good signal and over three is a bad thing.

Jason Calacanis: 30:21 You spend two million, you make a million, totally fine. You spend three million to make a million. Okay, that’s not super efficient. What’s going on here? And are you going to catch up next year?

William Barnes: 30:31 Yeah, exactly. And so I, you know, there’s a certain group of founders where you get the investor updates and they’re being very kind of disciplined about how they start to increase spend. And again, it’s sequencing. It’s like, do they feel like they’re really starting to solve a customer problem? Do they have they then been able to prove that they can start scaling that through sales or SEM? And only then do they start to increase the spend relative to how much money they have in the bank.

Jason Calacanis: 30:55 Signs, or thoughts about constraint. You tipped us off to a little bit of it. Constraint, 5 at 5.

Amanda Bradford: 30:59 5 at 5. I mean, we also only launched in San Francisco. We’re only in San Francisco for the first two years. So we made sure we really understood that market and had a good product in that market prior to expanding. I think the other piece for me was time. I don’t know, a lot of founders are wired like me where perfection is the enemy of done, I always say. And it’s easy to just sit and spin and want to keep perfecting things. So by setting a launch date and saying we are going to launch on this date and telling your customers that, that forced us to actually get the product out, or else I could have tried to make it perfect forever. So I always say to founders, give yourself a deadline however you want to do that, whether it’s telling your customers when you’re going to launch, but I know that’s what got my butt into gear.

Jason Calacanis: 31:21 So you have geographic, you have financial and timelines, you have the ratio of spend to revenue. Yeah, you also have maybe a waitlist and limited availability as a constraint.

William Barnes: 31:31 Yep, you then have a social contract.

Jason Calacanis: 31:34 Social contract.

William Barnes: 31:35 Yeah. We were talking about a really interesting, beautifully designed app about helping people find friends and get out in the real world. And you and I were brainstorming about it and I said, you know, I wonder if, you know, there’s a possibility of having two day-parts, you know, the brunch lunch period and nighttime. So that means seven days there’s 14…

Jason Calacanis: 31:54 It’s a lot of liquidity to…

William Barnes: 31:56 Yeah, to fill. You have 14 events occurring. I wonder if you took the peak loneliness, which probably occurs for people on Friday and Saturday night…

Jason Calacanis: 32:29 Not Amanda. Incredibly popular, but for you and I, sitting home Friday and Saturday night, like we’re losers. We text each other and go get a drink or should we go get some sushi? We’re losers no more. But…

William Barnes: 32:44 But I wonder if they just focused on Friday night, Saturday night, Sunday brunch, and that would be 3 of 14, and just nailing that, selling it out and creating pent-up demand. That would work so much better than this open platform where everything can occur at any time and then nothing occurs. what you’re saying is you’re touching on several points we’ve talked about which is what you’re doing is you’re nicheing down and so now your marketing communication or how you pitch it to people can be more narrow right so it’s easier for them to understand because it’s constrained and then your ability to serve that product is easier because you’ve got you know a narrow more narrow scope so you’re going to spend less money and make it easier for you to deliver on the promise.

Jason Calacanis: 33:23 When you put it all together, you don’t need as much money, your ability to execute because you’ve narrowed the constraint, you don’t have to spend as much time so you can get customer feedback quicker.

William Barnes: 33:35 Yep. And you can like nail the product more easily.

Jason Calacanis: 33:38 Correct.

William Barnes: 33:39 Because it’s not… I don’t think you can just do a good job. You have to absolutely nail it and like over-deliver if you want to drive word of mouth.

Jason Calacanis: 33:54 So those five people Amanda have to be really high quality in your example, in this example just that came up in two different conversations just hey what if there was only four events on the weekend with only eight spots each now you’ve only got to fill 32 and you’re going to crush them and just make each of them so wonderful and great.

Amanda Bradford: 34:06 And it also prevents like for us you know as a consumer marketplace you’re going to have the cold start problem so I knew from the get-go I was like I’m not going to have nearly the liquidity that someone like Tinder does and so by limiting that by only showing you five people don’t have to know that maybe there’s only 15 people total you know I buy yourself you buy yourself a couple days to give them you know give them your full set of inventory so you don’t they don’t have to know how small the the pool is at the beginning.

Jason Calacanis: 34:29 I’ve been thinking about that myself reflecting on Founder University in the United States it was getting popular and popular and I said hey listen there’s no cost to accepting more people we should be just able to scale this and we did 350 people the last time and then what we found out was because we had 10 pods there was 35 people in each pod the great founders would skip the pod because the pod was being filled up with questions that were so rudimentary from the people who were just very early or neophytes or maybe not even cut out let’s be candid to be founders and I said huh did we know that coming in and we’re like we kind of knew that some of them weren’t ready maybe we’re just being a little too…

William Barnes: 35:12 Sure version of the gym selfie dudes no kidding.

Jason Calacanis: 35:14 Yeah exactly like maybe just too many people and trying to do more so I I asked the team hey can we do less.

William Barnes: 35:18 Yeah. And your team is now spending less time with the best people right because they’re more distracted.

Jason Calacanis: 35:22 Right because they’re more distracted with the squeaky wheels who get the most grease and so in Saudi we did 60 here we did about 30 in Founder University and then it makes the pod smaller so then we had a really interesting question what’s the optimal number of founders to be in a pod every Thursday night talking about their startups and we came to well two or three is probably too small 30 is way too big so between those two numbers we think the right number is it might be 15 it might be 10 it could wind up at 20 but it’s enough that everybody gets to participate and there’s no cameras off so the number’s probably eight nine or ten is my guess but we don’t know we’ll figure that out but we are enforcing constraint which I think is pretty cool. Interesting. Next up we want to talk about distribution, we’re cooking with oil right now. First up we talked about product first, let’s put the fundraising down the road, and we’re going to keep that burn rate low in order to do that. Customer obsession and meeting with customers and understanding them, that costs you zero dollars. Most founders are too scared to do it, if you’re too scared to do it, you can’t be a founder, you should quit now. Number three, feature creep, death march, doing too much, and why are you doing too much? Well, maybe you don’t want to focus on your customers or build the product. Trust is just so critical, reliability. And then constraints, our fifth item. Now we’re at distribution. How’d you handle distribution, Amanda? And how do you think about distribution today? When’s the right time to be thinking about distribution? And I’ll include virality there, I’ll include paid, I’ll include social, I’ll include everything. Just distribution as a concept. Some people might refer to it as go-to-market, some people might call it growth hacking, but just getting distribution for your product.

Amanda Bradford: 36:59 Distribution is everything. So that is your main, primary job as the founder and CEO is to figure out if there are distribution hacks for your product and you gotta go find ‘em. So, um, if you’re not the one doing marketing, you should be at the very early stages. For us, you know, we found a combination of doing events, inviting press to events, and then pitching press were actually our biggest levers and they were all somewhat free because the events didn’t end up costing that much money. We were able to get bars and restaurants to sponsor or to say, ‘Hey, you can do this for free if you bring x number of people to our bar on a Monday night when they don’t have anyone.’ So we were able to kind of find hacks to get that initial, you know, couple thousand people in the database. And then we found a playbook. So what we found is that as we went to cities, we would get local press, so, you know, Dallas Morning News, San Francisco Chronicle, you get these local publications to write. For us, the tagline was, ‘Tinder for the elite is coming to your city.’ And so we would run that playbook over and over again for each city we went to and press was our best friend.

William Barnes: 37:54 And it was controversial.

Amanda Bradford: 37:56 Oh, 100%. Don’t be afraid to push against, uh, you know…

William Barnes: 37:58 You, you actually agitated it. You knew it was coming, and you said, ‘Hey, this event is only for people who can get into the League and it’s elite,’ and they were like, ‘Oh my God, we’re gonna count the demographics and we’re gonna write this,’ and you can go look up these pieces.

Amanda Bradford: 38:11 Yep, we were the first ones to reject people from a dating app. So it was a, you know, it was a controversial concept at the time.

William Barnes: 38:16 Which makes it worth writing about. So you figured out how to hack local PR and national PR.

Amanda Bradford: 38:22 Yep. Journalists were our best friend. Today, in today’s era, that would probably be influencers, you know, if you can find people with distribution on Twitter, on Instagram, on TikTok. If they’re gonna be talking about your product for free, that’s amazing. If you can get people to just try it. So inviting those people to events, those kinds of things. We… Business Insider was our best friend. Yeah, they were doing clickbaiting and all of that just got people to know the domain name.

Jason Calacanis: 38:49 Zillow did something similar. They created a very controversial device. Not, you know, apply to become part of the dating site. It was the Zestimate. This is our estimate of the cost of your house. People got really upset. Your estimating the cost of my house, it’s wrong, my house is worth more. Everybody thinks their house is worth more.

Amanda Bradford: 39:06 Right, you want to see what your house is valued at, right?

Jason Calacanis: 39:08 Plays into vanity. Plays into vanity, plays, yeah, and if something’s wrong, people want to fix it. The same thing the Wikipedia had, which was sometimes the China page originally when I first started using Wikipedia was one paragraph. And people were so upset that like your like, this is the largest country in the world and it’s one paragraph? This is an embarrassment. And they said, okay, hit the edit button.

William Barnes: 39:28 And they were like, okay.

Jason Calacanis: 39:31 The population of China is… and like then the next person was like, okay, you don’t have anything about X, Y, and Z, let’s add that. And Zillow then made local reports about the zestimates of the local and the national and then to this day, they send out reports every week, a different city or geo gets sent out so that their team can rotate from, you know, Arizona to Texas to New York, really amazing way to get distribution.

Amanda Bradford: 39:55 Yeah, it’s a vanity play.

Jason Calacanis: 39:59 Give to get worked pretty well for Uber. Perhaps too well, yeah?

William Barnes: 40:04 Yes, definitely. Uh, at times they have… there were groups of people that were hacking it. They would create landing pages and then drive SEM traffic against it to sell them.

Jason Calacanis: 40:15 They were buy ads to go to a landing page. In fact, my friend who I introduced Uber to…

William Barnes: 40:18 I know this story.

Jason Calacanis: 40:20 He bought, my friend Nick, bought ads on Google that said Uber is now in Los Angeles, click here to get a free ride to get $25.

William Barnes: 40:31 Oh, I remember, I remember this guy.

Jason Calacanis: 40:34 And it was one or two dollars per click. He converted like every other click, so it’s $4 and every time he got $25 credit in his account. He got to like three or four hundred rides and he’s like ‘it got turned off, I lost all the things, but I spent all this money, can you get Travis to undo it?’ and I was like, yeah, let me bother Travis with you hacking the system against the terms of service. No. But give to get, that was of the moment.

William Barnes: 40:47 It was definitely of the moment. I mean, and I think the… the specific example which you can turn into generalized advice is that your existing power users or people who love the product are the people that are most likely to be able to talk to and find other people that are going to love the product.

Amanda Bradford: 41:08 They’re advocates.

William Barnes: 41:09 Yeah, they can… you can turn them into advocates. If you have a customer that loves your product and is using it a lot, it’s worth spending time with them and incentivizing them to find other people in their life that are like them.

Jason Calacanis: 41:19 There were… I think there was a moment of time where people were building tools to take their eBay listings or their Airbnb listing and get it onto Craigslist. And they built tools to just have that happen automatically and have it happen in different cities. And then it was like a little cat and mouse, Craigslist trying to do it. But building these little tools that help people move inventory from one place to the other was enough to just make this work. And the people who had Airbnbs, well they would set up their own landing page and send people to Airbnb.

William Barnes: 41:55 I mean, it’s… I think it’s a pattern that I’m guessing all three of us… It’s insane is, you know, 10-15 years ago building the technology was equally if not the hardest part of the start-up.

Amanda Bradford: 42:06 That’s just six months.

William Barnes: 42:07 Yeah, it took six months. And I think with, you know, I think the term that all VCs like to throw around is Jevons Paradox, you know, as something gets cheaper, people use them more. And I think that’s definitely true with AI and low-coding, and so the product piece is getting easier.

Jason Calacanis: 42:15 Jevons paradox.

William Barnes: 42:16 Jevons paradox, things get cheaper, people use them more. And I think that’s definitely true with AI and low-coding, and so the product piece is getting easier. I mean, obviously, truly brilliant products are still hard, but it is easier to build product now. And so I think there is more and more value being created in distribution. And so that can either be, you know, the obvious example is influencers, people with podcasts…

Amanda Bradford: 42:42 Yeah, but Dropbox is a great example where, you know, you’re sharing with a friend and then they have to create an account to get access or the classic…

Jason Calacanis: 42:51 DocuSign. DocuSign is the best one. If you do DocuSign, it’s like we can save, this is saved in your locker. If you ever want to look it up again, and then you’re like, yeah, I gotta get that document. Is it still in my locker? Yeah, don’t worry, it’s in your locker.

William Barnes: 43:04 But distribution can mean different things, right? So the obvious one is, you know, an influencer, somebody with a big audience. But distribution at an early stage can mean other things like access to customers, you know, an industry insider, somebody that’s worked inside an industry…

Amanda Bradford: 43:21 Hiring someone with a Rolodex.

William Barnes: 43:23 Hiring somebody with a Rolodex, an advisor, an early angel that has got deep relationships in an industry that you want to go and sell into. So they can help you go and find customers to go and do customer discovery with is another good example. And the other one is a design partner. And a design partner is, you know, kind of an anchor customer that’s going to allow you access to their workflows, their data. They’re essentially saying, like, hey, you’re building a product, I will let you use my data, or I will kind of commit to giving you feedback and having access to…

Amanda Bradford: 43:52 …and in return for testimonial, right?

William Barnes: 43:54 Yeah, exactly. And so they’re different forms of distribution.

Jason Calacanis: 43:57 And that product council is what it used to be called in enterprise software.

William Barnes: 44:00 Customer council, yeah, product council.

Jason Calacanis: 44:02 Customer council, product council. It’s like people would, I remember when I was inside Sony for 18 months, one of the few jobs I was able to hold… 14 months, now that I think about it. Anyway, I got asked to be on like the Cisco one or this one. And all it was was a local sales rep just trying to figure out how to take us out to more lunches and bond with us so they could sell us more stuff. But we got to say that and put it on our resume, so on my resume I had, ‘Oh, I was part of this council, that council’, and then, ‘Oh, tell me about that’ when I go to my next job. It’s like, ‘Oh, they thought so highly of me I got to see their new products first.’ This is really amazing.

William Barnes: 44:41 And you own the relationship, right? And so if they’re trying to find, with Sony you were working at?

Jason Calacanis: 44:46 Yeah.

William Barnes: 44:47 So if they’re trying to sell into Sony somewhere, they’re going to ask you for an introduction. They’re going to, if they find a route into a decision-maker, they’re going to ask you to forward an email…

Jason Calacanis: 44:56 They literally asked me for the corporate directory. And I was like, ‘I don’t think I can give that to you’. They’re like, ‘Yeah, no, we’ve got it many times’.

William Barnes: 45:00 Yeah, exactly.

Jason Calacanis: 45:00 It’s like, okay, yeah, I guess maybe I could… what are you looking for? And it’s like, well we need somebody in Jersey, you know, who does this thing. My gord, we’re having a great time in Tokyo. This is our second time as a group here. William, I took you last time, which was your first time coming here, so…

William Barnes: 45:15 Great French toast.

Amanda Bradford: 45:15 And karaoke.

William Barnes: 45:17 And pizza.

Jason Calacanis: 45:17 Continue, go ahead.

Amanda Bradford: 45:18 And sushi, of course.

Jason Calacanis: 45:19 And…

William Barnes: 45:21 Wild boar and bear. Yes, Smash Burger.

Jason Calacanis: 45:24 The Smash Burger was exceptional. Wagyu Mafia. Wagyu Mafia was great.

William Barnes: 45:28 Yeah.

Jason Calacanis: 45:29 Tonkatsu.

William Barnes: 45:30 Pretty great. Pretty much all the food.

Amanda Bradford: 45:32 Wagyu Mafia was quite expensive. But…

Jason Calacanis: 45:35 Yeah, I gave you that bill.

William Barnes: 45:36 We thought it was in Yen but it was Dollars.

Jason Calacanis: 45:39 Yeah, it was pretty disturbing. And she… Amanda’s like, ‘J-Cal, you’re paying for everything. I’ll pay for Wagyu Mafia.’ I was like, ‘Okay.’ It’s just a Wagyu Sando. And they charged her $350 for a sandwich with gold leaf and caviar on it.

Amanda Bradford: 45:51 Times three. Yeah, because we had three.

Jason Calacanis: 45:52 Times three, so she got hit with a $1,000 Wagyu bill.

William Barnes: 45:54 It was very yummy. It was very yummy.

Jason Calacanis: 45:56 But I always love introducing people to the culture here because… …gosh, the commitment to excellence.

William Barnes: 46:03 It’s wonderful.

Jason Calacanis: 46:05 It’s just wonderful to see people take… …the doughnut as seriously as the car, as seriously as the consumer electronic device, as seriously as the hotel… …as seriously as when we lost our bags, Amanda. And we were frustrated and then we had this moment of like, okay, let’s put our entitlement aside. If we were in America and we had lost our bags, we would be in a 12-person line with the woman behind the counter… …who was extremely upset at us.

William Barnes: 46:26 For being there.

Jason Calacanis: 46:27 For existing. But I gotta say, there was a lady with my name, she had my name on a sign.

William Barnes: 46:31 She went to find you knowing your bag didn’t make it.

Jason Calacanis: 46:34 Yeah, and they asked you to describe your bag.

William Barnes: 46:36 In detail. In a lot of detail.

Jason Calacanis: 46:37 What color is it? What size?

William Barnes: 46:38 Does it have a zipper? Does it have a lock? Does it have the code?

Jason Calacanis: 46:40 What material is it?

William Barnes: 46:42 Very meticulous.

Amanda Bradford: 46:44 Very meticulous.

Jason Calacanis: 46:45 And then William and I started joking, what would the next five questions you could ask us? It was like, are you happy with the bag? Have you considered other bag options?

William Barnes: 46:50 When did you first meet the bag? And we were just like, wow.

Jason Calacanis: 46:54 This woman cares so much about getting Amanda her bag. J-Cal didn’t get a sign.

Amanda Bradford: 46:58 I think I don’t know Japan that well. I’m not gonna pretend to know the culture that well.

William Barnes: 47:00 But your second trip, you’re now an expert.

Jason Calacanis: 47:03 But my second trip, so I’m now an expert.

William Barnes: 47:05 It does seem that unlike in the United States… in the United States, there is social status associated with the job itself. Like, what job you’re doing has social status. My limited observation here is that there seems to be social status… …not about the job, but how well you do the job. Correct.

Jason Calacanis: 47:19 And craftsmanship.

William Barnes: 47:20 Yeah, your competency and the detail and your enthusiasm for pursuing excellence.

Jason Calacanis: 47:21 And in order to do that, leads us to our seventh point, which is the team and team building. What’d you learn, Amanda, in your years of team building, and tell us the mistakes? So many mistakes. That’s a different podcast, probably.

Amanda Bradford: 47:32 I’ve spent different… But team is everything.

Jason Calacanis: 48:01 Yeah, okay. Great. Everything is everything. Product is everything, distribution is everything. We always say everything is everything.

Amanda Bradford: 48:08 Well, I was just saying for me it was the hardest thing to learn and it’s the easy to ignore it at the beginning. You’re so focused on the marketing and the product and, you know, those are kind of the glamorous things front of the house and then actually building and retaining and hiring and firing if people aren’t working, and being able to fire fast when it doesn’t work. Those are actually what really should be taking almost 30% of your time in this zero to one stage and it’s easy to ignore it and spend maybe 10% of your time on that.

Jason Calacanis: 48:35 Where did you find great people and how did you assess their greatness and potential?

Amanda Bradford: 48:40 Well, my favorite story is my first employee, Meredith, had to email me I think five times because I’m not great at responding to emails all the time. And so she learned quickly that she needed to follow up with me and she was one of the few candidates that followed up enough to get the job.

Jason Calacanis: 48:54 Founder candidates. Persistence, grit, not, you know, not being offended because someone didn’t write you back. I’ve had people like that.

Amanda Bradford: 49:02 No, understand that the founder’s busy and they’re going to go the extra mile and step up to, you know, get the job done. And so I think people that are willing to raise their hand and, you know, go the extra mile.

Jason Calacanis: 49:13 William, what have you learned over the years in terms of talent and finding great talent, inspiring great talent and maybe cutting talent that isn’t going to do their best work at your company?

William Barnes: 49:25 I mean, I think hiring for depending on if you’re talking about hiring an early stage company or…

Jason Calacanis: 49:31 We’re talking about early stage company, first two years.

William Barnes: 49:33 Yeah, then I would focus heavily on generalists that have incredible attitudes and like high slope.

Amanda Bradford: 49:40 That was my first hire.

Jason Calacanis: 49:42 Let’s define and unpack high slope.

William Barnes: 49:44 High slope is somebody that you think has kind of the… they’re open-minded, they’re highly conscientious, they’re low on neuroticism and it’s the type of person that you can throw at multiple problems and they’re just going to go and figure it out. They’re not necessarily going to be, you know, a domain expert and become like a VP of engineering, but for the years where you are early and you’re trying to find out solutions to random problems and there’s pivots and there’s chaos and you’re working late and there’s psychological drama…

Jason Calacanis: 50:11 Yeah, no, there’s fear, company could go out of business, it’s not working.

William Barnes: 50:15 No resources. Most really good founders are pretty obsessed and they can have quite sharp elbows and you need people around that founder that can handle that and so that’s why low neuroticism is so helpful because they’re not going to get derailed by those things and they’re pretty steady and they’re highly conscientious and they can grow into solving different problems.

Jason Calacanis: 50:37 And they can juggle, right?

William Barnes: 50:38 And they can juggle and they’re high energy. They’re people that are like intrinsically high energy and they’re like learning machines.

Jason Calacanis: 50:47 And they’re not going to get frazzled when you say, hey, we’re going to Tokyo and we need to find an AV crew to record the episodes and we need to get really unique food and I want to do…

William Barnes: 51:00 swag and they’re like they don’t say I don’t do that.

Jason Calacanis: 51:02 Yeah.

William Barnes: 51:03 They’re like oh okay well let me ask ChatGPT and Google and Gemini and like how would I do this if this is going to be true what would need to be true?

Jason Calacanis: 51:11 Yeah. I think there’s a fearlessness to certain individuals who if they’re built for a startup culture we call them Jack of all trades or Janes of all trades in the United States but it’s somebody who will understand hey we’re a five person company there’s eventually going to be 20 people here doing 20 different jobs but right now there’s five people doing four jobs each and maybe at best we each know two of those jobs but we’re going to on the fly figure out paid marketing on the fly we’re going to figure out how to find the restaurant and how to do PR because I assume when you did all this great stuff on PR you didn’t have a PR firm advising you?

Amanda Bradford: 51:46 No I figured it all out and then I gave it to Meredith once I figured it out and she would go

Jason Calacanis: 51:50 And Meredith was an assistant to you? Like your assistant?

Amanda Bradford: 51:54 She was everything from an executive assistant to doing customer support to doing marketing to sending emails to our customers to doing Facebook ads to talking to you know partner restaurants and bars to get an event done she did everything that I had to do.

Jason Calacanis: 52:05 So let’s that’s not always true

William Barnes: 52:07 but I have seen time and time again someone very young yeah someone very young that hasn’t like they have come from a flyover state and they have made their way to LA New York or San Francisco.

Jason Calacanis: 52:19 Interesting archetype flyover state

William Barnes: 52:21 Very precise. They didn’t they didn’t necessarily go to an Ivy League school their parents definitely didn’t go to an Ivy League school.

Jason Calacanis: 52:28 So they’re hungry.

William Barnes: 52:29 They they probably had jobs in high school and certainly worked in college.

Jason Calacanis: 52:33 Working class.

William Barnes: 52:34 Yeah.

Jason Calacanis: 52:35 Blue collar.

William Barnes: 52:36 And they played sports in in college.

Jason Calacanis: 52:38 So discipline. With the with the sports.

William Barnes: 52:40 Yeah and they’re very competitive.

Jason Calacanis: 52:42 And you were one of those people. They hired you as you were from the flyover state of London.

William Barnes: 52:47 Yeah exactly yeah the backwater.

Jason Calacanis: 52:51 It is now it’s now London has kind of evolved into a flyover.

William Barnes: 52:55 Well it’s like we’re going to Paris or Germany we’re going to Dubai I don’t know if you want to go to Paris or Germany I think you just keep going

Jason Calacanis: 53:00 No just go right to

William Barnes: 53:01 Right to UAE.

Jason Calacanis: 53:02 Yeah.

William Barnes: 53:03 Yeah we’re not sending our students to London it’s too radicalized.

Jason Calacanis: 53:05 It was the greatest headline ever.

William Barnes: 53:06 Amazing my parents yes I sent that to my parents.

Jason Calacanis: 53:11 Right it took me three times to read that to understand what I was reading.

William Barnes: 53:15 Yeah.

Jason Calacanis: 53:16 The world’s changed.

William Barnes: 53:17 It looked like an Onion headline. Well I mean and in all honesty those kind of people are just so valuable to the company especially early on.

Jason Calacanis: 53:25 Later on they get called special projects… fixers.

William Barnes: 53:29 Yeah.

Jason Calacanis: 53:30 Because

William Barnes: 53:31 As the company gets bigger you you know for better or worse you get specialization.

Amanda Bradford: 53:37 And you have to take things away and you have to have people that are okay with giving away some of their power and not taking that personally or you know wanting to keep their power base.

Jason Calacanis: 53:45 Go ahead and tell me how you would say that to Meredith hey we’re taking PR away from you you did it you had this great success

Amanda Bradford: 53:51 Well she was great at that so I put her in that but I took her away you know

Jason Calacanis: 53:55 So you specialized her to that.

Amanda Bradford: 53:56 Yes that’s where she ended up staying but like at the beginning she was customer support she was doing our mail because I hated checking the mail she would actually send the mail to my mom.

Jason Calacanis: 54:00 It was some downtime about but she might have loved customer support. How do you say, ‘Hey, we’re taking this away from you, you didn’t do anything wrong’?

Amanda Bradford: 54:05 Yeah. But there’s this actually great First Round Capital article called ‘Giving Away Your Legos’. And so I had everyone on the team read that, and it’s just about as you scale, you are going to have to give away parts of your job and that that’s a good thing, that’s not a bad thing.

Jason Calacanis: 54:17 In fact, a great founder is literally trying to get to the state where there’s nothing… they come to the office on Monday, there’s nothing left that they… they have to do. That’s when you actually know you’re successful I think as a founder is that when you take a week off, the company does as well or better than if you were there.

William Barnes: 54:34 Yeah. What I’ve seen work well in terms of taking projects or scope away from people is first of all understanding what… what their kind of career goals are. Do they want to stay a generalist and stay early stage? And if they do, then like it’s time to get off, you know, the train and I’ll help you find something.

Jason Calacanis: 54:49 We have a four-year vest for a reason.

William Barnes: 54:51 Yeah, and if you do want to specialize, which is I would say 75 to 80 percent of the time they want to specialize… Okay, which area do you want to specialize in? Okay, so this… okay, well my job is to go and find an expert with much more experience than you. They’re going to come in over you, and their job is going to be to mentor you and help you achieve their career path. And I’m not going to be able to do that because I’m not a 15-year marketing expert. But my job is to find someone that you find inspiring. And if I don’t hire that person, you’ve got every right to turn around and tell me I’m an idiot and I’ll help you find another job somewhere else.

Amanda Bradford: 55:25 Yeah. And the good ones will stay and the bad ones, that’ll make them leave because some people don’t want to get hired over…

William Barnes: 55:31 They’re delusional. Like if they… if you think, you know, you’re four years out of college and you know you’re going to become a CMO of a series…

Jason Calacanis: 55:39 Happened to me on a board. I was on a board and they said we want you to be on the audit committee. And I looked at the founder and I was like I’ve never done anything like that. He’s like ‘Yeah, I just think it’s an opportunity for you to learn’. And then, you know, whatever, you fast-forward two years, I learned how the audit worked, I learned how to interface with the accountants and I was like ‘God, exciting stuff’.

William Barnes: 55:53 I see that as your superpower, Jason. When I think of you, I think auditing.

Jason Calacanis: 55:57 I know. It was the worst two years I had to go through but I was like, you know what? If this is what the founder of that company in New Hampshire, Dyn, wants me to do, I’m going to be loyal to him and suck it up and do it. This was 20 years ago. But I said ‘Okay, you gave me a board seat, I’m doing it. I’m going to make this work’.

Amanda Bradford: 56:13 Yeah, yeah. And that’s not one of the points here, but just learning to delegate as a founder. I know I struggled with that. I kind of liked owning things and I wanted to do it and you have to really learn to give work away and be okay with the fact that maybe it won’t get done exactly as you would have done it, but 80% of the way is actually good enough in startup world. And so you have to learn how to delegate.

Jason Calacanis: 56:29 One of the great things about delegating professional development that I’ve learned is it will lower the anxiety in the organization of ‘If this person leaves, the company’s effed’. ‘Issue! This is all coming off the rails’. So what we do is I will say, ‘Well okay, you’re running Founder University until this date. Six months later you’re going to work on the syndicate. Six months later you’re going to work on the fund. Six months later…’ Later you’re going to go work on first calls with founders and running that department. So there’s your 24-month experience. GE used to do this and I rotate and we do professional development and when the person hands it off to the next person I say do a Zoom call, record it, put it into our Notion database, and make a document with all the instructions, use AI to summarize it. Now when we’ve done the first handoff of, hey you’re handing Founder University off and you’re going to work on the accelerator, now you’re leaving the accelerator you’re going to go work on the syndicate, each time you hand that off, now we’ve done it two times or three times, now there’s two or three calls, Zoom calls on that page now. The first time was handed off, the second time, the third, so the next person who gets handed off to can watch all three of those.

William Barnes: 57:46 You’re creating documentation which is write first culture, is how we say it, how Amazon says it.

Amanda Bradford: 57:52 That was one of our values, write it down. Whoever writes it down gets credit for the idea.

Jason Calacanis: 57:57 It is a core tenet.

William Barnes: 58:00 I’m going to steal that.

Jason Calacanis: 58:01 It is true. All right listen, this has been over an hour, what an amazing episode. We will take two questions, please.

William Barnes: 58:09 So there are a lot of folks in this room who will make money, some who won’t. All three of you have gone through the process of making money. I’m curious how has the meaning of money changed in your life as you’ve accrued more? Money, I mean you’re both going to laugh at me for this, money has non-linear value. Each incremental dollar you get becomes worth less than the one you had before and there’s probably some step function depending on your lifestyle needs. Money solves money problems and it just allows you to have more time to worry about other things or focus on things that I think are more valuable. I think having money is a bit like debt, it creates massive leverage and so it amplifies the person you are. If you know you’re the type of person that wants to spend lots of time with your family, you make a bunch of money and then you’re like oh I’m going to spend a bunch of time with my family now. If you like lots of external validation from social status games, you are now going to do that more. So it’s an amplifier. I think people need money obviously, but once you hit a certain threshold, acquiring more money is not about the utility it provides, it’s about kind of the psychology of it.

Amanda Bradford: 59:12 Lots to unpack. Um, I guess I would say it allows you to think bigger. I think at least for me with The League, you know that was sort of like all my net worth was tied up in this company. And so if the company, I don’t know, all of a sudden had a class action lawsuit and we were sued out of oblivion or all of a sudden, I don’t know, a new competitor comes out and wipes us out, I was nervous that like all my work would go to zero. And so I think you know by selling it and by earning enough to to sort of have a nest egg, I now feel like I could swing and I could probably take more risk. So you know, J-Cal’s just waiting for me to to pick a big idea to do that with but…

Jason Calacanis: 59:51 She guaranteed I’d be the first investor and William would be the second.

Amanda Bradford: 59:55 I have not said that.

Jason Calacanis: 59:57 To William. She hasn’t said it to William, she said it to me this morning.

Amanda Bradford: 60:00 allows you to get to whatever, you know, that, that ability to then sort of think bigger and think what would I do if money was no issue, right? And, and think about solving those kind of problems versus like how do I make X amount of money in my life. But yeah I think it kind of…

Jason Calacanis: 60:13 Definitely when you hear that term FU money, some people I find they get the money and…

William Barnes: 60:20 Go on sabbatical? No, I’m kidding.

Jason Calacanis: 60:21 No, but, no, it makes them more guarded, more anxious, it becomes a distraction for them, and then some people, a smaller group of people, it does actually give them the ability to say, I’m going to do things and pursue them the way I want to, with my vision, without compromise. That’s what it did for me. It just gave me the freedom to say, I’m going to use my own chip stack, I’m going to do it the way I want to do it. If anybody doesn’t want to do it that way, I totally understand, but I’m doing it my way and, you know, this purity of vision I think is very freeing. When you have a bunch of investors, when you have a board, you know, you have to build consensus and that’s good when you’re young because you’re going to learn a lot. And then there’s a certain point where you’re like, I think I know the playbook and I know what works for me. This has now given me the freedom that I don’t have to compromise the vision. And so that can send you off the rails. Francis Ford Coppola just did a film…

William Barnes: 61:13 Megalopolis.

Jason Calacanis: 61:14 Megalopolis, that nobody has seen, and he sold his watches and his vineyard and he made this perfect vision for him at the age of 80 or whatever.

Amanda Bradford: 61:18 He’s a documentary about it.

Jason Calacanis: 61:21 And it’s been a complete flop or whatever, but he wanted to make it, it made him happy, he’s not going to be here for much longer. Okay, more power to him. But there are other people who also, you know, they started to get a taste of that money and all of a sudden 20 years of their life went to a Marvel franchise or a Star Wars franchise. And George Lucas said he always wanted to make small, intimate films and then he just, Star Wars…

Amanda Bradford: 61:52 Got addicted to the money train.

Jason Calacanis: 61:55 And it just became bigger than him, right? And he never… who’s, who can tell me a George Lucas film that is not Star Wars?

William Barnes: 62:04 American Graffiti.

Jason Calacanis: 62:05 After Star Wars? Sorry. Tell me a film he made after Star Wars. He had a really hard time doing that, so it became a burden. So sometimes the success can then be a burden. I have that now, I mean, podcasting I do is so successful, and Tim Ferriss has been going through this, Lex Fridman went through it. The podcasts that they did became so successful they had a hard time having other things in their life that they wanted to pursue. So Lex was telling me he wants to do a startup, I think he’s been pretty public about that, and he’s trying to balance being a famous podcaster, making tons of money from the ads and doing that. Tim Ferriss I saw just tweeted, ‘Do you want me to do more podcasts or do you want me to do less podcasts with higher video production?’ and you know, when I saw it I was going to text him, I’m going to text him, ‘Do what you want Tim, I want you to do what you want. Now I want you to do more audio ones ‘cause I don’t care about video.’ But he’s looking at all the other podcasters who came 10 years after him and did this like high production value. I think he’s… knocked off his game where he’s like, ‘What do I need to do here?’ and ‘You need to do what you enjoy. Do what you love,’ right? That’s the freedom it gives you, and you don’t have that early in your career. You—

William Barnes: 63:13 I don’t want to presume the question behind the question, but, you know, if you read biographies of successful entrepreneurs who have made a lot of money when they’re much older, they all say, ‘I miss being young and building something, and I miss building something with a group of people.’

Jason Calacanis: 63:26 And not having the resources.

William Barnes: 63:27 Yeah, and like the money. It’s obviously a luxury statement to say they don’t care about the money because they’re very wealthy, so they don’t have to worry about the money. But they do—they all say the same thing, which is like building something with a group of people that you enjoy spending time with is the thing they miss more than anything else.

Jason Calacanis: 63:42 Here’s the other thing I’ll tell you. I realized this after a couple of friends of mine passed away. Me going skiing on the mountain, me owning a ski house. I own a really nice ski house. I can ski in and ski out at Lake Tahoe. And I ski 20 days a year in Lake Tahoe. And then there’s somebody else who does 50 days a year and they’re broke. They bought the same epic pass I did for 800 bucks, you know, season pass, and they get twice as many days as me, three times as many days as me. I’m jealous of that person. They get to ski three times as much. And I was trying to explain this to somebody like, when I go to dinner with Elon, myself, and then somebody who’s broke and then somebody else, the steak that we order tastes the same to everybody. And there is an upper bound in almost all of these things that you can buy. And we both drive the same car, a Model Y, because it has full self-driving, it’s the best car ever made. But he also owns a really nice Porsche, and I’m buying this super nice Corvette hypercar and it’s like—

William Barnes: 64:18 Thank you for your money.

Jason Calacanis: 64:19 Well no, I’m just like, but I’m not going to drive it. So I talked to him about his Porsche, that was his dream car, and you’re selling it now.

William Barnes: 64:50 I’m selling it. And so that tells you everything you need to know. It’s like, 15-year-old me is very pleased that I bought the Porsche, and now 46-year-old me is like, ‘Okay, done.’

Jason Calacanis: 65:01 Done. Check box and you move on. It’s a great question. Another amazing episode. Thank you to William Barnes, thank you to Amanda Bradford, thank you to our friends at Jetro, and congratulations to all of the great founders in the first cohort of Founder University. If you want to learn more, go to founder.university. You’ll see a link for Saudi, Tokyo, Japan, and the U.S. programs. Apply. What do you got to lose? Maybe you’ll be the next founder that changes the world and that we invest in, and hopefully we can join you on that journey. We’ll see you next time on This Week in Startups. Bye-bye.