Jason's ultimate dream mega-purchase + Founder Q's | E2228

This Week In Startups is made possible by: Northwest Registered Agent- https://www.northwestregisteredagent.com/twist Vanta - http://www.vanta.com/twist Lemon IO - https://lemon.io/twist Today's show: Jason's already a millionaire many times over… but what are the huge, blockbuster, dream purchases that he's still holding off on? BESIDES the private jet we all know he wants? The Noti Gang has asked, and JCal finally answers, on a holiday TWiST where we're taking questions from viewers and fans. Check out the episode for lots more intriguing queries, like how to push forward and glean useful information when your first customers aren't using your product the way you'd envisioned. Plus, is there room for both AI agents and great SaaS startups in the coming years? Hear why Jason thinks there IS. AND we've got the very last Gamma Pitch Deck Competition entry before we announce our winner in the new year. Check out AskHumans, an innovative approach to improving market research. Timestamps: (00:00) On a special holiday TWiST, we're answering YOUR pressing Founder Questions! (8:35) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today! (09:35) What should a founder do when a VC reaches out cold? (13:37) The importance of maintaining "ball control" (15:35) A European founder asks: Should I take European investments if they're targeting American customers? (19:47) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist (20:51) A member of the Noti gang asks for JCal's dream mega-purchases (24:12) Why Jason thinks there's room for BOTH AI agents and great SaaS companies (27:18) Lemon.io - Get 15% off your first 4 weeks of developer time at https://lemon.io/twist (28:23) It's our final Gamma pitch with Zak from AskHumans! (29:24) How AskHumans uses AI to improve on marketing surveys and research (34:33) Management and measurement were designed before computers could understand language… why this matters. (35:48) Why no one ever wants to give feedback in a video (39:01) Why Zak's pitch is "two chapters of the same story"… and was this a pivot? (44:14) Why founders need to assume LLMs are going to get exponentially better * Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com/ Check out the TWIST500: https://twist500.com Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp * Follow Lon: X: https://x.com/lons * Follow Alex: X: https://x.com/alex LinkedIn: https://www.linkedin.com/in/alexwilhelm/ * Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis/ * Thank you to our partners: (8:35) Northwest Registered Agent - Form your entire business identity in just 10 clicks and 10 minutes. Get more privacy, more options, and more done—visit https://www.northwestregisteredagent.com/twist today! (19:47) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist (27:18) Lemon.io - Get 15% off your first 4 weeks of developer time at https://lemon.io/twist 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 Aaron Levie https://podcasts.apple.com/ca/podcast/box-ceo-aaron-levie-breaks-down-box-ai-and-generative/id315114957?i=1000612384545 Sophia Amoruso https://podcasts.apple.com/ca/podcast/sophia-amoruso-on-branding-raising-a-fund-portfolio/id315114957?i=1000601352978

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  Now that you're doing so well financially, what is a purchase that you'd like to make, but can't bring yourself to do so because it feels too extravagant? Answer this honestly. Tell the people what you, even Jason Kalikandis, will not break out the checkbook for.

• 0:12Jason Calacanis?

  It's definitely private aviation. I've been trying to hold off on doing this for a long time. The great unjustifiable expense of spending $50,000 going somewhere or $100,000 on a round trip. That seemed absurd to spend that. The other one I would say that I sometimes sweat is buying a really expensive sports car. I love Corvettes and I really want to buy a barn dominium, which is like a big, open fancy barn. That's kind of like a man cave, but Texas style. Do I buy this ZRX1 for $250,000 or do I buy five $50,000 Corvettes and have a little collection? A lot of these things become cognitive load.

• 0:54Speaker 02

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• 1:37Speaker 02

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• 1:45Speaker 00

  Today's founder question, Jason, comes from our dear friends over at the r/startups subreddit. And I found a question that I had absolutely never seen before. So I thought it was the perfect thing to bring to us today. From our dear friend Entire Chest, quote, "I signed a $20,000 paid pilot, but it's a shark bite problem." Interesting framing. Shark bites are big crises because you're bleeding versus a mosquito bite, just kind of an irritation. They found a big problem to solve. What they did was they found that there's trucking companies that transport fluids. And often they get the wrong fluid in the wrong truck or the wrong truck goes to the wrong destination. And so they made a product to fix this and they signed a $20,000 pilot. They found a problem in the market. They made a solution for it. And then they went out and did more market research and discovered

• 2:27Speaker 00

  that other people in the fluid trucking industry don't have this problem. They seem to have found a uniquely messed up first customer. And so I was just really curious, how common is it to accidentally index on the wrong customer and drive in the wrong way?

• 2:41Jason Calacanis?

  This is why you want to get two or three customers and validate it across them. If one person says like, yeah, you know, we, we have milk containers. And if somebody puts gasoline in them, it costs a hundred thousand dollars. We, it's not worth cleaning them and puts them out of service for two weeks. So we, we gotta make sure nobody accidentally puts gasoline in here and it's a shark bite. It's like, you know how rare shark bites are? That's why when people are wondering like, why don't we have shark nets everywhere? Why don't we have shark repellent? Why don't we have more shark? It's because it doesn't happen that often. Now, in places where it has increased, and I love the shark bite versus a mosquito bite. Mosquito bite, let me tell you something, out here in Texas, it gets pretty gnarly in the summer.

• 3:25Jason Calacanis?

  You're going to sell a lot more of those candles and I have four, four electric mosquito bite killers in the house in the summer. Just the act of going inside and outside of your house lets mosquitoes in. I have these electric things, man, I hear this zap when these things, when we murder mosquitoes in the house. I leave them on and in the summer, it's like every hour you hear one of them get fried. Now you don't see them, they don't bite you, but it's because they probably just got in somehow. There's more money spent on mosquito bites than there are in shark bites. But shark bites, man, my feed on Tik Tok and Instagram is all shark bites, bulldogs and Japanese food. Why? Because I always watch a good shark bite.

• 4:08Jason Calacanis?

  I, as far as I'm concerned, people are getting bit by sharks 10 times a day. And that's not what's happening. It's happening three times a month. It's happening 50 times a year, a hundred times a year. Maybe it's a hundred times, I think there's two or three fatalities a year. And I think there's like a hundred or 200 bites a year. Somebody check as producer Claude. The reason is it becomes top news. Now, in a bunch of places now, I think Indonesia, where there are a lot of bull sharks, and Australia, where there's bull sharks, great white sharks, tiger sharks, every shark loves Australia, they are putting shark nets in, and there's even shark circles, which are places to swim in the ocean that have a net

• 4:53Jason Calacanis?

  around them and you can jump into. This is like, I'm super fascinated by this technology. It's two different technologies. One is, so six fatal unprovoked shark attacks per year.

• 5:05Speaker 00

  Which is not many.

• 5:06Jason Calacanis?

  So, one every two months. Every 60 days, somebody gets taken out. I don't know how many, 60, 70 bites a year from sharks. Yeah, so I think the shark bites are more. But, okay, sure. US, Australia, South Africa, Brazil, that's where it's happening. US because of Florida, and the number of people going in the, in Florida is the main reason. Florida's a lot of coastline, and people are in the water constantly there. But I don't think those are the fatalities. I think fatalities, Australia wins hands down. Some lunatic jumped into Sydney Harbor. This is dumb for three reasons. One, tiger sharks are known to feed in there. Two, it's polluted. Three, there are ferries and boats everywhere. If you

• 5:46Jason Calacanis?

  want to die, one of three ways, like a bacterial infection, a shark bite, or getting hit by a ferry, by all means, jump into Sydney Bay.

• 5:57Speaker 00

  How much money to get you to swim across Sydney Bay?

• 6:00Jason Calacanis?

  A billion dollars, I wouldn't do it.

• 6:02Speaker 00

  Oh, wow, really?

• 6:03Jason Calacanis?

  I might do it for a billion, because you didn't put any conditions on there. I would do it under a billion, and I would create a net that goes underneath me and around me in

• 6:11Speaker 00

  Reasonable conditions.

• 6:13Jason Calacanis?

  I might, let me think about that. For a billion dollars, tax-free cash.

• 6:19Speaker 00

  I'd do it for 10 million.

• 6:20Jason Calacanis?

  I wrote, actually, a science fiction story. I was thinking I would do screenplays at some point, and I had this scene, was kind of like a running man kind of take-up or a dystopian future, and one of the scenes was, in order to pay back their debts to society and to their victims, hard Criminals who were on death row could swim across the channel in South Africa where those air jaws were from one pontoon to the other in chummed water. And if they made it across, they would be released from death row. And at the same time, all the pay-per-view ratings, because they would have a GoPro on their head, there would be underwater cameras.

• 6:58Speaker 00

  It's just gladiators.

• 6:59Jason Calacanis?

  It's basically gladiators. But modern day, they would be forgiven and all the money would go to the victims. So if it made a hundred million dollars and there were 10 swimmers, or there are 10 victims and one swimmer, you get 10 million each. And the swimmer gets a million bucks and gets let out of there.

• 7:15Speaker 00

  We could call it Shark Tank.

• 7:16Jason Calacanis?

  Shark Tank. There it is. To our founder, yeah, you made, you learned a mistake. And then I think what you have to do is just the honorable thing to do would be to tell the person, listen, we're happy to finish this for you. We'll give you the source code. We can give you an employee to work for you. We can train one of your employees for a hundred thousand dollars. We'll make this bespoke software for you for the next two years or 250K. We'll do this bespoke thing for you, this solution, raise the price to the point at which either it becomes super profitable. Maybe one of your employees goes and takes it and does this bespoke software. Bespoke software is going to be the future, by the way. The fact that you can build software so quickly because of AI now, where you can build hardware so quickly because of Shenzhen

• 7:56Jason Calacanis?

  and all this commodification of batteries and chipsets and Arduinos and accelerometers and the iPhone, all of that means you can build bespoke businesses that make but a million dollars a year. And you have a 50% margin. You know what? For two people, it's good money. It's good money. And when you can't get a job at Meta or Google, that's the future. That's why you come to Founder.Under University. Now occurring on three continents, the US, F12 starting in March, Saudi currently underway, and our new one's coming. Go to Mina-launch.co, and our Japanese version, everything available through links at Founder.Under University. Man, this thing's growing.

• 8:33Speaker 00

  Yes, it is. Yes, it is. You're a busy, busy boy.

• 8:35Jason Calacanis?

  Being a founder is a lot of work. You have to focus on your fundraising. Then you gotta hire the perfect team. Oh, gosh, product market fit, finding your first customers. But all of this means nothing if you're not. Actually, a real business that's structured properly, giving your investors and clients the confidence to partner with you. At launch, we're constantly recommending Northwest Registered Agent to our founders because for just $39 plus state fees, they will act as your registered agent. That means they take care of all the paperwork, making sure your business remains compliant, protecting your privacy, and more. And as a founder, hey, man, there are so many organizational odds and ends that you have to worry about. So why not have a partner who can focus on all those little details? Then you can obsess about your customers.

• 9:19Jason Calacanis?

  And Northwest Registered Agent is even going to help you set up a phone line, a professional email account, and find you a great domain name. So here's your call to action. Go to northwestregisteredagent.com/twist to get your company set up the right way.

• 9:36Speaker 00

  So Jason, one of the best questions I've seen asked around founder communities in recent weeks is what to do when VCs reach out to you? We often spend our time talking about how people should reach out to VCs, but sometimes the tables are turned. Now, in this case, Mr. Cheetah over on the Venture Capital subreddit had built a really cool open source application, hit 1.8 thousand GitHub stars, and suddenly people are reaching out to him. He doesn't know what to do with this. He's not quite sure what he should prepare, what they're going to expect of him, or really just even the kind of Ps and Qs of dealing with cold inbound venture interests. So hit me with your top tips for founders who are dealing with VCs knocking on their door.

• 10:12Jason Calacanis?

  So VCs will hire associates, researchers, analysts, and they'll charge them with, "Go find me some interesting companies." Now, some people have a lot of inbound. I happen to be in that group. Y Combinator, Techstars, Sequoia, you're going to have a lot of inbound. Later in your career, when you're established as an investor, you get a lot of inbound. But when you're starting out, you need to get something going, and you want to have proprietary deal flow. As an investor, you need to master three Ds.

• 10:47Jason Calacanis?

  You need deal flow, you need to make good decisions and you need to know when to double down. So deal flow, how did you meet Uber? How did you get Robinhood? How did you get Calm? Where did Grin come from? Then, did you make a good decision to place the bet? And then finally, did you double down on that bet when you had a chance? And then my fourth D is distributions, DPI, pick which one you want. So those are the four Ds. And to be great at venture capital, you need to source a company like Grin. You can go look at grin.co. This is one of our accelerator companies that became worth a billion dollars. We made the decision to invest in them because we believed in influencers as a marketing strategy 10 years ago when they came to the accelerator. Here's grin.com. Company's

• 11:29Jason Calacanis?

  doing phenomenal. It's been a great, great company investment for us. We doubled down. We invested in like three or four rounds of this company, not just from our fund, but when our fund was done investing and we'd hit our targets as a seed fund, we gave it to the syndicate. Then, so we had great deal flow. They came to us. They applied. We made a great decision to invest. We made a great decision to double down. Then, when it hit a billion dollars, there were people who wanted to buy some of our shares. We made a great decision to sell, I think, 17 or 18 million dollars in our shares during peak ZERP.

• 12:03Speaker 00

  Ah, nice.

• 12:04Jason Calacanis?

  Now, let's go back to the original question. Somebody's trying to get deal flow. You need to know who that somebody is. In all likelihood, it's not Sequoia or Andreessen Horowitz or Y Combinator reaching out to you, which means it's an up and coming VC. Does that mean you shouldn't listen to them? No. It means you should get curious. You should research them. You should put it into a database. You should have a CRM tracker of every VC that reaches out to you and you should figure out what companies they've invested in. Now, it is important that you not be distracted when you're building your company. So you don't want to be taking meetings with VCs, in my estimation, unless you're raising. And a great way to handle this is to say, we're not currently raising. We don't have time to meet because we're busy building, but we plan on raising in Q4 of next

• 12:49Jason Calacanis?

  year. A good time for us to talk would be Q3. Then if, you know, if you neg them like that, they're gonna be 10 times more interested. I will give a caveat here. There are nefarious people who are doing this in an automated fashion and they're just spamming anybody with a Crunchbase profile, an Angel List profile, you know, on some list. And so you will get spam and you will get people who look like investors who are maybe trying to sell you something, real estate, maybe they're a broker. If you can't figure out who this firm is and who the person is, they don't have a LinkedIn page, they don't have a profile page, just throw it away, don't even respond. If it's a legitimate firm and you can say, hey, they have these other investments that

• 13:32Jason Calacanis?

  are interesting, great, but do not give any information. And you can say, I'm too busy to meet, but this is a good time for me to meet. Now you have ball control and, you know, that is like super important. You have pot control in, you know, a poker game, in a poker hand, you have ball control in a football or basketball game, you're kind of controlling this conversation. And you're the founder, you have to understand you are the precious resource in this, not the investor. The investors are a commodity in, I'd say 70% of investors do not add any value and in some cases they detract value.

• 14:07Speaker 00

  The Vinod Khosla argument, yeah.

• 14:08Jason Calacanis?

  Vinod Khosla has said this many times. And so the top 10% of investors, they can be very helpful. I can be very helpful. You know, Sequoia can be very helpful. Chamath, Saks can be very helpful. There are specific people, Steve Jervis, very helpful. Brad Gerson, Altimeter, when he dips into privates. These people can be very helpful for obvious reasons. They have incredible networks and they, if you can get through their filter, become a, you know, real validation for your startup that they would take the time with one of their bullets to, or one of their bets to place it on you. Fantastic. But these are going to generally be unknown firms, unknown quantities. So therefore you stack them. And then what I would do back when I was an entrepreneur,

• 14:53Jason Calacanis?

  I'd say, well, we're based in Santa Monica. I'm not meeting with people, but I will have time, you know, two months from now in this week. If you want to stop by for coffee, to have a quick coffee, you know, for 30 minutes, I can do it in February. And so it was December now. I'd say, yeah, second week in February, boom. And I would just, again, back to getting ball control. And I'd say, you know, thanks for your interest. We're not raising right now, but this is when I can meet if, and I would make them come to my office. They say, oh, can we jump on a Zoom? And say, yeah, I'm sorry, I don't have time for that.

• 15:19Speaker 00

  And how popular was that?

• 15:21Jason Calacanis?

  You know, I was able to raise the Series B before I launched the company famously, and was able to raise $20 million in a time when that was a lot of money and significant to raise. I had a really good idea, really good execution. So this is the best advice I have for this person.

• 15:36Speaker 00

  Next question comes from the Entrepreneurship subreddit. I found a really interesting question that I'd never seen actually asked before, Jason. And I want to get your take on this because we have talked about a number of European companies. We also heard about a lot of people coming over from Europe to build in the United States. So here's a unique situation. This founder, they're from Europe, they're building in the United States, their target market is for young professionals in US urban cities, but they're getting a lot of traction and interest from European VCs. And they say, we keep hearing the same thing. Do not judge the VC's money, but judge their ability to help you succeed. So what are people's thoughts? Is it a bad idea to take money from the Euro VCs when their target market is America? And I have a thought about this, but I was just kind of curious, what would your advice be here to this founder?

• 16:18Jason Calacanis?

  You know, there are great venture capitalists all over the world, and they do want to have, you know, they're just looking for great companies. So sometimes you'll have a European VC that only invests in Europe, and they'll be very clear about that on their website and their marketing. And they have other ones who are, you know, Australian VCs, or European VCs, or Singapore VCs, or Mobodila, you know, in the UAE. And they're just looking for great companies. So there's no downside. And if they've got a great reputation, and you vet their reputation by doing backdoor references,

• 16:53Jason Calacanis?

  From their CEOs, that's the best reference. So if you wanted to know if I was good, you would ask somebody at Uber, Robinhood, Calm, Grin, et cetera. Hey, what was it like having Jason as an investor? Did he show up for you? Did he introduce you to people? Did he add value? And so when I train my team, I'm like, these backdoor references are happening and we never hear about them or we rarely hear about them. And sometimes we do, you know, sometimes somebody will say, hey, this person called me to ask you. And I'm like, wow, that's a sophisticated investor. Before they took our money, they asked another founder. Other times, VCs will say, hey, here are three founder references. You can call these three people and ask them about us. So that's basically what you want to do. You should be doing as much or more diligence on your investors as they are doing on you.

• 17:36Jason Calacanis?

  And that's something that founders forget because they get a little enamored when you're early in your career by VCs. Then later, experienced founders become cynical about investors. Oh, they're just a commodity. It's just money. Who cares? Just take it at the highest price. The truth is somewhere in between. Don't be enamored by them. Don't be intimidated by them, but also, you know, don't devalue them because they could be the person who gives you that one piece of advice, one connection or accelerates the business in some way. And that's what the great investors do. But you had a take on it. What's your take? I'm curious.

• 18:10Speaker 00

  Oh, my, my take is that, you know, if you have great traction from European VCs who are going to have an extra amount of interest in you because of your European heritage, take advantage of that. Like this is the thing to capitalize on, not to be worried about. If they can't offer reasonable terms or they offer a lower valuation than you want, then, then cut them loose. But I would say if you have an edge, ride it because right now the market's very competitive and it seems that it's kind of feast or famine in the startup scene.

• 18:34Jason Calacanis?

  The other thing is you might be the best deal that they are going to get into. Whereas, you know, in, for Sequoia in the heart of Silicon Valley, you might not rise above with Sequoia's deal flow, but you might be the top of this firm's deal flow. And that's not a dig to the, to Europe in any way, but they may just have missed, you know, I don't know, Anthropic or XAI because they're not in the mix and they're not here and they didn't know about the Palantir round and just got closed and. Fund grabbed it. So they might covet you in a way that, hey, maybe Founders Fund is too busy for you. Sequoia is too busy. They've got too high of a bar and you didn't hit the standard that YouTube and Instagram hit for Sequoia.

• 19:17Jason Calacanis?

  So, you know, now you're number one with them. So, great question. And all money's green at the end of the day.

• 19:22Speaker 00

  I mean, Lovable just raised from Minlo and Capital G. It's still based, I think, in Europe. So if American investors can back Europe, to me, yeah.

• 19:30Jason Calacanis?

  It's all about quality, right? I think what you're saying here is Lovable is a quality company. They happen to be in Europe. Got investors from America. There could be investors over there who are quality investors who want access to American companies. Yeah. Great, great deals and great investors are not constrained by geography. Startups move fast and in the age of artificial intelligence, they're moving faster than ever. But moving quickly doesn't mean you can fall behind when it comes to security and compliance. Hey, move fast. Let's break things. Good advice at times, but not exactly what huge enterprise customers want to hear. So that's why I recommend Vanta to my founders. Let Vanta worry about your SOC two and your HIPAA requirements.

• 20:13Jason Calacanis?

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• 20:53Speaker 00

  All right, Jason, pulling from our dear friends in the Nody gang, RoyalYon31, I think that's how you pronounce that, wants to know that now that you're doing so well financially, what is a purchase that you'd like to make but can't bring yourself to do so because it feels too extravagant? And if you say the jet, I'm going to say no repeating yourself. So answer this honestly. Tell the people what you, even Jason Kalakandis, will not break out the checkbook for.

• 21:15Jason Calacanis?

  Oh, gosh, it's definitely private aviation. You know, I Well, I've been trying to hold off on doing this for a long time. But as my time gets constrained and I become more successful, the great unjustifiable expense of spending $50,000 going somewhere or $100,000 on a round trip, that seemed absurd to spend that. It can also at some point seem absurd if you have a certain amount of income and a certain amount of net worth to not buy $500,000 a year in a jet card, which would be 50 hours. And it doesn't make logical sense, but if it does make your life easier or your family's life easier, yeah, that's the number one one.

• 21:59Jason Calacanis?

  The other one I would say that I sometimes sweat is buying a really expensive sports car. So I really covet this. I love Corvettes and I really want to buy a barn dominium, which is like a big, open fancy barn that's kind of like a man cave, but Texas style. And I love Corvettes and I've been on this Bring a Trailer website or Cars and Bids website, watching Corvette C2s and C3s going by and C6s, my three favorite gens. And I'm like, do I buy this ZRX1 for $250,000? Or do I buy five $50,000 Corvettes and have a little collection? And so those would be high net worth problems.

• 22:42Jason Calacanis?

  But you know, a lot of these things become cognitive load. And so I like to stay humble. I like to not have cognitive load. And what I find is every time you own another home or you own another asset, it just becomes like a little bit of load on your processor. And so I had two properties in California that I rented. And so they now become income properties. I wanted to sell them, but they were coveted properties, so I rented them instead. But now I have to worry about those. So I like the stay focused on the thing. And the thing is really just two things for me.

• 23:22Jason Calacanis?

  Being on podcasts and talking and then two, investing in companies and hanging out with those founders. Everything I do that's not that becomes cognitive load. And does it actually add value to my life? That's what you really have to, that's what you really have to, you know, wring your hands about. So it's obnoxious to even talk about this kind of level of stuff. And I'll be honest, putting, buying a $50,000 1970 Corvette Stingray would give me some joy, but putting two 25K first checks in Founder University would give me more. I'll be totally honest. So that's what I try to, you know, stay humble and stay focused. I'm 55. I'd

• 24:04Jason Calacanis?

  like to put another 10, 20 years into this. And yeah, if I'm going to put 10 or 20 years into it, it's important to not get distracted by earthly possessions.

• 24:13Speaker 00

  Jason, over in the notice, our dear friend Pilgs wants to know, what is a common industry belief that you currently disagree with? Or what is the biggest risk that you're taking right now?

• 24:23Jason Calacanis?

  I would say the application level of AI is something I believe is going to provide massive value and SaaS enterprise software will continue to provide massive value. I do think the industry's down on these things because they think that, you know, the large language models will wipe those things out. I kind of think the opposite. There's always a way to create a more refined product that solves a singular problem for a small group of people and you add features and community and design that speaks to that group. So as an example, when we made the investment in calm.com, the meditation app, people were like, why would you invest in that? You could just get meditation videos for free on YouTube,

• 25:05Jason Calacanis?

  which is true. You could talk about Tonebase or Musician or Steezy or Brilliant.org. All of those are educational type vertical apps that have had massive success. Fitbod as well. You know, but again, people said, well, you can just learn how to play an instrument on YouTube or for free, or you can buy a book or this or that. Why would I need a verticalized one? Well, if you look at those verticalized ones, Tonebase and Fitbod as just two and Brilliant.org, they're so dedicated to those verticals of, so here's Tonebase. They know who the best classical violinists are, you know, clarinet players, trumpet players.

• 25:51Jason Calacanis?

  If, you know, this is something that OpenAI is not going to get to. There's something YouTube's not going to get to. Could you find on Instagram or TikTok how to play, you know, a Louis Armstrong trumpet solo? Yes, you're going to be able to find that. But if you want to go deep and you want this trumpet player and you want to take it to the highest level, Tonebase is the place to go. If you pull up brilliant.org as an example, you know, could you learn how to do some math problems from Khan Academy or other places on YouTube for free? Of course. Could you have ChatGPT explain it? Yes, but brilliant.org is going to verticalize these and they've gamified them. And man, these questions are so well thought out.

• 26:33Jason Calacanis?

  And the, the way they've done personalized learning here and adaptive learning, they're just going to have a nuance and a fit finish and polish that those other platforms aren't going to have. And what happens is people will use the large language models, get to a certain point, and then they're going to want something more. If you're charging low hundreds of dollars, why wouldn't you spend it? You can get calories from any number of food sources. That doesn't mean people are not going to spend, you know, $50 on an amazing, you know, steak from Long Hill Wagyu or Miyazaki Beef. They're, they're going to want that as well, even though they can get hamburgers for, you know, from Shake Shack for nine bucks. Okay. I think, I think I made the point. Maybe I beat the point to death.

• 27:18Speaker 00

  No, no, I beat the point to death.

• 27:19Jason Calacanis?

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• 28:00Jason Calacanis?

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• 28:25Speaker 00

  All right. Next up, we have a gamma pitch. It's time to bring Zach Kidd from AskHumans up on the show. Jason, this is our final gamma pitch. This is number 10 of 10. And don't forget, we'll be backed in the new year to crown a winner and that person will receive a $25,000 prize slash investment from both Launch and Gamma. Zach, welcome to the show, man.

• 28:44Speaker 03

  Thank you so much, Jason. Nice to see you. You look great. Texas is treating you well. I can see the sunshine is hitting your face.

• 28:49Jason Calacanis?

  Yes, I'm sometimes getting too much sun, but yes, I'm I'm svelte. I'm well rested. I'm rocking. I'm peptides. I'm GLPs. I got everything going on. Ro.co, shout out to my friends over there who are providing me with my GLPs. So AskHumans, really interested in getting the update here. So we'll give you two minutes on the clock for your presentation. If you go a little over, that's okay. Three, two, go.

• 29:11Speaker 03

  AskHumans is a platform that helps organizations collect open-ended feedback and act on it at scale. So this is Jenna. She is the Director of Membership of the Neds Club, which is in Washington DC. The Neds Club is owned by Soho House. Now, these high-end membership private clubs, when they're really trying to understand what members think or what staff thinks, really, they have collected information very anecdotally in the past. Basically through conversation, what's been heard in the lobby. And the challenge of that is really to sort of speak to ownership and speak to management in terms of how they should run their club better so that members are happy.

• 29:54Speaker 03

  So we've worked with them over the past four months and we've integrated Ask Humans into many points throughout the club. So they have brass stands on every kiosk. They actually have Ask Humans embedded into their iOS app. So when members open up that app, they can give feedback. They also, when you check out and you and you get a check, our QR codes are integrated into their POS system. They're effectively now able to really understand what people think within their clubs at scale. This is Jenna speaking to that.

• 30:27Speaker 04

  Humans is such an incredible tool for us to be able to gather member feedback all in one place and have a live sentiment analysis of what our members are happy with or what they're disappointed in. We deliver our transcripts by department on a weekly basis to our teams so that they understand exactly what our members are saying. And then on a monthly basis, we get together and review everything and develop action items to make sure that we are always listening and responding to what they want.

• 30:57Speaker 03

  So I really appreciate Jenna sharing that with us, really showing how they're integrating Ask Humans into their operations. Jason, they're now actually extending Ask Humans into London, New York, and potentially even Dubai. But what we are doing is we're taking this open-ended feedback technology that we're integrating and we're actually building an entire suite now of applications that could integrate more deeply into any organization. So we are bringing together a calendar in which you can look at your day and then sort of gather feedback from your colleagues. We are also doing meetings. So we've basically cloned granola so that you can record conversations that integrates into your workflow. One of

• 31:40Speaker 03

  the big things here, Jason, is that we really believe that feedback given LLMs can now more deeply engrain into an organization's team and workflows. So it's not just external feedback, it's internal stakeholder feedback too.

• 31:55Speaker 03

  Additionally, we have loops which are reoccurring check-in questions for your team to give feedback. That runs on cycles. So let's say it kind of replaces your stand-up where where where members can where your team members can give feedback and could see what's changed from one week to the next week. And then, of course, studies which runs with all of our clients and then also something called presentations. All of this. We're we're building with the ability for you to talk to the data and actually to listen to personal podcasts as a summary of all the feedback that's coming along. And our clients are loving this. So the Washington DC Economic Partnership is using AskHumans now.

• 32:35Speaker 03

  Where they're integrating it into their workflow. So whereas before they were sending surveys or hiring consultants to understand what the public thought about economic development. Now, every outreach phone call they do to a tenant broker or to a company, ask them, hey, how, why would they want to come into Washington DC? They're recording that with AskHumans. That's being transcribed and integrated in. That's being paired with the studies that they're doing to collect, you know, overall feedback. And of course, that's also sort of integrating into the presentations and what they're showing alignment around feedback too. So the last slide here is just, of course, you know, this look at as information that's public becomes zero cost to attain.

• 33:19Speaker 03

  Any information that any organization can gather, which is novel and non-public, is incredibly valuable. We've basically built the suite to allow teams to gather open-ended feedback that's not found anywhere else and then to act on that.

• 33:36Speaker 03

  We've done over a million minutes in recording over the past 10 months. And we're just loving the success that our clients are having. And again, just thanks a lot to Gamma for sponsoring this and Jason, thanks a lot for your time.

• 33:50Jason Calacanis?

  Wow, platform has really come together. There's internal products that do this. We are investors in one for a long time, 15.5. And that's performance management of team members, rollups, very sophisticated, you know, based on like Google. Philosophy, et cetera. And then you have surveys, like famously Survey Monkey and other ones that people will roll their own. You're building an AI-first solution here. And so that means you have to displace the one that the NEDS using, or most customers you go to, they are not using this and the AI is giving them sort of a reason to engage with it because it's more powerful. Which is it? Are you displacing people typically, or are you coming in and it's like blue ocean?

• 34:36Speaker 03

  This is a totally new capability for some of the organizations that we're working with. Generally speaking, when you think about measurement and management, the practice of management and the practice of measurement is generally rooted in computers not understanding language, right? And so with management, you have management by walk around. The CEO actually having to sort of walk around or that, you know, the Steve Jobs having lunch at the cafeteria to hear from what his employees think. Or if you think of measurement, you're sending out a survey and you're asking people on a scale of one to 10, what do they think? Well, of course, all of that occurs because it's rooted in computers just tabulating, not understanding language. And so it's a complete blue ocean when you, when you understand operationalizing the fact that computers can now understand language.

• 35:20Speaker 03

  And so measurement and management is absolutely being rewritten with a platform like Ask humans.

• 35:25Jason Calacanis?

  All right, final question, and then I'll give it over to Alex. Do, in the case like a private club like the NED or, or even in an enterprise, do people prefer to give audio, text, or video feedback? What, what is the modality that people prefer most? Do they like to be anonymous? Do they like to have their name attached to it? Because, you know, they, they want to close the loop on it? Or do they just want to send it into the void and just make sure it's heard?

• 35:50Speaker 03

  One thing people hate is video. No one wants to do video. And one, one thing that people love is the audio. One, it's multilingual. Two, it's super easy to multitask. And three, people don't want to think about, you know, how to sort of exactly, you know, phrase what they're, what they're saying. They just want to talk. I'll, I'll, I'll give you the one, one tidbit. We work a lot with the Department of Buildings in Washington DC, they have gathered 7,000 responses from over 40,000 of permit applicants at Department of Buildings. They basically have a 60% increase in their feedback through Ask Humans than to

• 36:32Speaker 03

  than to previous systems. It's really quite, and that's to the general public. That's not like one specific cohort of people.

• 36:39Jason Calacanis?

  Does the AI ask a follow-up question? Or is that not, is that, is it too early to do that with, you know, fidelity?

• 36:46Speaker 03

  We released, thank you for that softball question, Jason. I appreciate that. About three, about three months ago, we actually built in AI follow-up. Again, everything is configurable. You asked the question about anonymous or non-anonymous. We really let clients choose. If it's anonymous, maybe because you're asking, you're doing a town hall with all of your employees and you're the World Bank and like, that's what they've used. Maybe it's non-anonymous because you want to be a little bit more customer focused and you want to follow up. So it's, it's really totally configurable on the client's perspective.

• 37:17Jason Calacanis?

  Yeah. So they can click a button and have the AI basically predict or make a prediction as to what's the best follow-up question. So if somebody says, hey, the club is far too crowded and there's not enough staff to, you know, get food out in time on the weekends. They could say, okay, have you experienced this at other times? Or is it just on Friday and Saturday nights? It could, yeah. Or is it specific to the bar or specific to the tables? It could come up with maybe a good follow-up question. And as long as it doesn't do something embarrassing, I guess, why not give it a shot?

• 37:51Speaker 03

  Yeah, it's, it's been really great for, for, I think with, you know, clients really love that personalization at the end user perspective. And end users really like it because they recognize that they've been heard. And at the end of the day, we all want to be heard.

• 38:02Speaker 00

  Yeah. Zach, so going back to the presentation itself, watching this as someone who's new to Ask Humans and didn't have a lot of prior context. I would thought we were going one way to start with presentation. Here's a club. Here's a, you know, a little brass plucker with a QR code. Collect feedback. And then it felt like there was kind of a hard pivot over to the enterprise use case. You know, the granola functionality and that sort of thing. So just thinking as someone who is de novo to it, that is maybe a place you could bridge a bit more and explain how the club example maybe better fits into the rest of the other features because it did seem slightly distinct to me. Does that make sense?

• 38:39Speaker 03

  Oh, it's definitely two chapters of a longer story.

• 38:41Speaker 00

  Okay, so is the first couple of slides then, is that still core to what the company is doing? Or are you now more focused on kind of the internal context of helping companies better understand their own staff?

• 38:51Speaker 03

  Alex, when we launched studies, we launched studies really for to be to gather external feedback for organizations. And what we found specifically with the World Bank is they used our studies for their own internal staffing to gather feedback from their global staff around the world. And then we saw that and we said, okay, we know that there is a straight line with using studies for external feedback, but there's an entirely new set of opportunities for for collecting internal feedback and really allowing for organizations to collaborate around the best ideas that that people have. And so that's why we established loops and presentations and meetings.

• 39:31Speaker 03

  And when you think about how all of this can interconnect into one platform, imagine if every client call you have, plus the studies that you're doing on a monthly basis, plus the presentation you sent potentially to a prospect. If all of their verbal feedback can can come onto one platform that you can then interact with, that's a very powerful and entrenched solution that really drives collaboration and knowledge forward for that organization.

• 40:01Speaker 00

  So instead of me thinking this is really two different products that seem to be sitting next to each other, you think they actually are quite connected and you really want to have both the internal and external feedback in one place to learn from it at the same time.

• 40:12Speaker 03

  That's exactly what's happening.

• 40:13Jason Calacanis?

  Got it. Yeah, that makes sense. Yeah, it's such a new concept that you've got feedback coming in, you know, at this private club or at this government agency. Then you've got the feedback coming in from employees interpreting that feedback and just how their jobs are. And it becomes this nonstop, continuous feedback loop. Now, of course, management. Has to decide when to listen to things and when to ignore things and when to ask follow up questions. So none of this is like you're going to blindly follow it. But if you start thinking about the job of managing an organization, feedback is critical. And then what happens in these organizations is feedback becomes politicized. So a CEO asks for feedback and

• 40:57Jason Calacanis?

  then feedback comes in, it gets massaged, and then it gets massaged again, and then it gets presented in a way like as the seventh item. And this is why I always insist in our organization that the feedback for everybody who speaks at the accelerator or Founder University, etc. gets ranked by the people who heard this talk. And then that gets put in a database and we just track it over time. And my instructions is, you know, just it's shared by everybody. It just posted into a Slack room. There's no filtering of it when it gets to me. And we give it to our speakers, even if they get a low rating. And we will then tell them, hey, remember, we told you in rehearsal, or we asked you to do a rehearsal and you skipped the rehearsal?

• 41:39Jason Calacanis?

  We think this 6.5 could really be a 9.5 if you just did one rehearsal with us and we talked about it. So yeah, the that's going to be like the key to the software in my mind is can it be available to everybody in the organization? And can it not be and just for founders who are listening, you got to be really careful that nobody shuts off access to feedback. I've been in organizations where the customer support person has the keys to the kingdom and they give like a roll up report. And it's like, nope. I and I had people, oh, you don't need to get feedback at. And I'm like, no, I want feedback to come from me as the CEO of the venture firm. And I want it to come from my personal email address. So every founder we meet with, we send

• 42:24Jason Calacanis?

  them a survey. The survey comes from my email address. And it says, this is a form letter you met with our team. But if you hit reply, it does come to me and I will see it. And I see all the results of our founder performance. And we ask founders, how likely are you to recommend our firm scale of one to 10? And we ask them for some color commentary whenever it's seven or less.

• 42:46Speaker 00

  It goes into one chat room and if it's eight and above, it goes to another one. Founder tomatoes or founder applauds or whatever it is with an emoji. And then we have a follow up system for it. So just, these tools are great. You've just got to make sure that nobody tries to massage the results to protect the guilty.

• 43:02Speaker 03

  I mean, I would just say, you know, your prior friend Ray Dalio at Bridgewater, you know, in radical transparency, like he ran his firm with, you know, honest, open ended, put your ideas ahead of you and let it be judged. So this is the type of culture that we're pushing forward. And in an age of AI where everything is being annihilated in terms of tasks, it's really what's in between people's ears. That is the most valuable thing that they could bring to a table. I'll also second, you know, going back to, you know, your hometown of New York City, back in the day, Theodore Roosevelt, when he was police commissioner, you probably know this story too. He would actually put a code on at two o'clock in the morning and jump into the police cars and talk to the police officers because he wanted that on that ground feedback.

• 43:45Speaker 03

  So now we're effectively able to sort of bring that feedback into what we say is collective judgment.

• 43:50Speaker 00

  Zach, can I ask one more tiny thing here? Just how, how good is AI at sentiment analysis? Because in a lot of your slides, you showed they're kind of red, yellow, green. And that to me seems so incredibly useful if it's accurate. So how confident are you in those sentiment analysis numbers?

• 44:04Speaker 03

  We've been, you know, we, we spend a lot of, we have a, we have a PhD at USC working on inference and how we're doing our eval pipelines. Yes, I am brushing my shoulders, it's not me. I think, you know, Sam Altman talked about this. When you were looking and probably for any founder out there, when you're looking to be in the space on the application layer, you should assume that the LLM models are going to get 50 times better and make sure that doesn't make your, your product less, less relevant. And at the end of the day, what you think Alex or what Jason thinks or what producer Marcus think, if you're able to sort of, you know, put that into Ask Humans, regardless of how good, as those models get better, we're just able to do better analysis. And so, you know, we're really, really excited, you know, every time from when we went from four to 5.0

• 44:49Speaker 03

  in terms of how our data is better and better as a result.

• 44:53Speaker 00

  All right, it's askhumans.com. And if you're feeling inspired, head to gamma.app and start working on an idea of your own. And maybe we'll see you here on a future episode of Twist. All right. Bye, everybody.