YouSaid · the spoken record

Jeremy Redman

lines on the record: 80
first: 2025-05-16
most recent: 2025-05-16
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“Active listening is a concept to say proactive. There is a concept called active listening in therapy and in the CIA and FBI and profilers, active listening, which is you're really thinking what the person's saying, how they're saying it, why they're saying it, but when you go from there.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“How do you ask quick questions? You got to listen to the answer. Listen, you'll listen to the previous answer and then you form your next question.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Basically, yes. I haven't been on high stakes poker TV in a while. I got to go back. All right. Listen, Jeremy, you're awesome.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“A business. Alex wants me to be able to say to him, Alexin, it's great working with you. I know you care about your kids greatly, spending time with them. You love your wife. You really care about journalistic integrity and fairness because you would even sacrifice your own salary when you were at TechCrunch to help the team And cautious optimism Really does embody what your passion is, which is to write every day and communicate these complicated topics. Like he knows I understand what makes him tick because I listen to him, you know.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Okay, so you're building a business that makes a more affordable version of common mission critical SaaS products and you're coming up with a new way to distribute it with these 2,800 affiliates and at the same time you're using a different business model that makes it easier and frictionless for people to give you money in advance of them using the product Do I understand your vision correctly, Jeremy?”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Hey, Jeremy, may I repeat back to you my understanding of what you're doing here in the business to make sure I understand your vision?”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Exactly. So that's like being a chess player, and you're just like, yep, I win. And it's like before it moves in. It's like, yeah, you made a mistake. And here's how it's going to end. That's not what they want to hear. You know, it's like a master Jedi with their Padawan or something. And they're just like, yeah, I just took off your two legs and your arm and, you know, game over. You got to like kind of slow down to speed up. So I just slowed down and I asked very simple questions. And I started pacing the founder. Founder had high energy. It was going fast. I go high fast. If they're going slow, I just ask them. And then I added something to the script when we meet with founders, Alex. Very simple. At the end of every call when they pitch, I wrote this script for myself and then I trained everybody.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“I did. There was the same piece of advice over and over again. Jason didn't understand our business And what it is is I process things very quickly so people felt like I didn't hear them out enough and I didn't understand their vision.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, and we try to be like if you think about what you need as a founder, like you need a quick answer and you need to make sure that we understand. Your company. And one of the things I realized early on was I started letting founders review us. So we sent them an email 48 or 72 hours after we do a meeting. And then it goes automatically into our Slack with the rating for each person. And it's public to the whole company. I got really bad ratings.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“In that Zoom call, the actual work of a venture capitalist at an accelerator or a pre-accelerator is doing 500 qualities a year, 1,000 calls a year with founders and checking in with them and, you know, whatever. So I optimized for that and you're experiencing that, which is I tell them hire people with enthusiasm. And if they're not fired up with enthusiasm, fire them with enthusiasm.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“And still have energy on the sixth, seventh, eighth one. So I then just said, I want to have people when they apply for this position of researcher, then they become analysts, then they become associates. I want them to just do a couple of calls and record the calls and then just show me the video. And then instead of hiring people based on what fancy degree they had, I just look at their energy on the video because the experience of a founder is the person having that conversation with you. Now, they have to be intelligent. They have to be bright. They have to be hardworking. They have to be disciplined. But they also have to be engaging on camera.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Interesting company. And I said, what's the most efficient way to do that? 20 minute introductory call, 10 minutes of you pitching us your product, five minutes of you asking us questions, five minutes of us asking you questions, and then we can both mutually agree on should we do another call and do we want to, is there any way we could work together? And so I said, how do we get to 100 of those a week? Well, you need people who can do five of them a day. Some people do eight a day.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“So I said to myself, okay, I need an army to sort and meet with folks. So I need to create a system. Remember, systems above goals. The goal is to back enough founders to find another Uber, Robinhood, and have those outlier power law investments pay for all the other ones. And on a philosophical basis, I want to be super helpful to founders and I'm passionate about innovation and all that stuff. But on a pragmatic basis, we need to hit a $200, $300, $400 company for every hundred we invest in because we want to have a three or four X fund. Okay, great. The math is the math. So we have to sort through a lot of companies. We have to meet with a lot of companies. How do you do that? We had this concept of an introductory meeting. What's an introductory meeting? We tell people, hey, we got your application. Would love to meet you and do a quick Zoom, which we can record and share with the rest of the team if it's a really”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Time we're like, I could tell you, I could teach you this. So I literally can teach you. I had a Realization when we're trying to hire talent. And I looked at the problem we had from first principles. We, as an early stage fund, have a lot of people coming at us with ideas, like upwards of 20,000 applications for funding. Second only, I think to Y Combinator, which has 45,000 applications. And that's because of the two podcasts, right? I say Foundry University. I say, hey, launch.co slash apply 100 applications come in we got to sort them”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Oh, we just started Week two pitching investors. Oh, we have those week zero, whatever. And how's it going with the investors? Bianca doing a good job, Erica doing a good job”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Perfect. So before you graduate accelerator, how are you doing in the, what is it, week six or seven in the accelerator right now?”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Perfect beehive. There's a bunch of free options So, all this legacy stuff, if MailChimp just said to me, hey, pay us 500 as you use it, it'll keep working, great. I would have done it. But, you know, so you're on to something, I love that you're on to something new. I'm going to tell you, pull the string and see where it leads you. Anyway, Jeremy, you got a great company. Can't wait to see you in person. Where are you based now?”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Think there's a lot of people who are open to this concept. You figured it out. You've got the passion for it. Let's go for it. Let's hope 19 of 20 investors don't understand it. That means you're onto something. If the people who are doing cookie cutter investing don't understand it, you don't need them. They're the people who would be like, do what has already been done. We're looking for something that has a small chance of working, but if it does work, changes the world. So I love it. I love the idea of you selling $100 in credits and use as you go. The reason I unsubscribe for MailChimp and I like literally, we still had one person holding onto their MailChimp account and I didn't realize it was costing us $500 a month, $6,000 a year. I was like, get off of that immediately.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Exactly. It's the lighting. It's the lighting. I work a little bit on the lighting. So, anyway, a new revenue model. And I told her, you know, like it's so much cognitive dissonance, this monthly bill and the subscription burnout that paying once. The guys over at 37 signals came up with a Slack competitor where you pay one time a thousand bucks. I'm sure you know about it and you basically pay yourself.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“A tribute website for a funeral, right? And instead of selling them per month per year, you just said pay $500 and we will keep this memorial on the internet for 50 years. Bucks a year for 50 years, past 500, you never have to worry going down, and you can put in the email addresses of your kids. They can put in their kids' email addresses and their phone numbers. And it's a family legacy, a tribute to on who we worked with and loved dearly. We went too early.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Me more. I like to consider myself in the non consensus Peter TL, Michael Moritz group, which is, hey, and Bill Gurley, what if it works? What if your crazy idea works? So as you've explained it to me, I'm so excited about it because I'm like, yeah, what if this works? And I was talking to another founder and they were in space? They were in a space where people would buy a piece of software or a piece of SaaS software for an event and they might use it for a year or two and then you kind of churn. And I said, well, what if you sold them this on a 50-year basis and you memorialized everything, you know, let's say I'm not going to, it's not this, but I'll make a thing like let's say it was like a”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Like robots are like, this does not pattern match the MRR turn formula that we have created. Who gives a f ab about those investors? You don't want those investors anybody. You want the visionary investors who are like,”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“I think you have a secret. So there is a theory in startups. I have a secret, right? The secret I've learned is oh, yeah, people will actually stay in another person's house and they're not the people who stay at five star hotels. They're young people or adventurous people who stay at Airbnb, stay at bed and breakfastes already or they couch surf on Craigslist. So you kind of know the secret. The founders of Airbnb knew this secret that there were people on the underground who would trade vacation homes or let people stay in their home if they could stay in their home. And they did there was like a house swapping kind of thing where you would come to New York and I would go to Paris and you stayed in my apartment. I stayed in yours. We vetted each other and it was all done on Craigslist, right? So you have a secret. Now most investors, if they're thinking.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“So tell me what is the question you have for me. I totally buy the strategy here. I think offering these things for free, collecting data at this stage since you seem to be pretty good at it, giving some money to the affiliates is a great idea. You've got this really interesting concept around that. Maybe the affiliate network is the business for other and selling that to startups. I would be interested in that if there was an affiliate network that sold tickets to events or got people to apply to Foundry University. I mean, that sounds very interesting as a distribution platform that you build for yourself. Or just getting a bunch of up and coming businesses to get a suite of products for one price. I don't know. There's something interesting here.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“So, this is a strategy of not just doing the email responses and competing with Intercom, but just going down the SaaS stack, creating simpler, cheaper versions and using this affiliate network to distribute it and get feedback on how to make the product better. So you're basically building a SaaS killing platform.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“And then you look at, I remember we used to set up mail servers, and then MailChimp came along and it was cheap, and then Beehive came along, and you could pay a flat rate fee and have your own domain name, and then Substack is free, but they take 10% of your revenue. Anyway, infinite options available. So that's a great strategy. What's the go-to market strategy for somebody trying to create something that's easy to use and super affordable? What is the pricing? And then I'm assuming the pricing is so low you can't have a sales team out there selling it, yeah?”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“On it. And so this is a tried and true competitive strategy. We're going to make something simpler, easier to use, more affordable for SMBs. If you were to look at a product like Salesforce considered like the gold standard in managing a sales team, you could come in with a lightweight version that's not. What a Salesforce cost per salesperson today. Is it like $2,000 a person or something?”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Pretty amazing. This is an incredibly competitive space. Why are you going to win this space in the face of so many competitors who want to attack customer support with AI”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Crazy. And so tell us about the new company. Give a little pitch here, elevator pitch, a really simple sentence, and tell us what you're working on now”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Rate it as asylum. And everything else, and it's just going to become bedlam. Just we want one million incredibly highly qualified people per year who create jobs to come to this country. The number's one million, I've decided. One million. That's it. Everybody could, I mean, a million people who create jobs and you have to create jobs. And if you don't, if you want to come here and you create 10 jobs on average, you can stay. If you create less than 10 jobs in five years, hit the road.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“It's all about framing. I literally was having this discussion with high profile people in and around the administration. And I just said, frame this as talent recruitment and job creation. You're”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Citizenship, just do the right thing. And then for everybody else, hey, if you're going to come here and create jobs, go get the Trump Golden, get the Trump gold card. You get 3,000 extra miles on United when”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Why don't we talk about that anymore? Like, NAFTA was this whole EU before the EU. The Republicans wanted an open border in the North and the South, right? They weren't the proponents and the architects of it. And everybody else just executed on it. So putting it aside, fight for this skilled immigration. And this is a very simple way to frame it. If you want to get everybody on board, America has to own, if it is a mistake that we let so many people and we have to own it. And we have to deal with it in a gracious, intelligent way. And the most gracious, intelligent way, and thoughtful way to do it and economically sound way to do it is to say, if you're contributing to our society, here's 10 years of taxes you need to pay and a path to citizenship and behave yourself like everybody else. Don't commit any crimes. And if you stay on the straight and narrow and you pay some taxes 10 years from now, whatever, we'll get you the green car. We'll get your citizens.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Of people came in. You can't make this a partisan issue. We're a country of immigrants. This country let people in across the last five, six, seven presidents since the 80s. Republicans were the biggest proponents of immigration and NAFTA, am I pronouncing that correct? Naftraft. Nefto North American Free Trade Agreement. We don't talk about it anymore. Neft tough.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“They all know, with the exception of maybe Stephen Miller and Steve Bannon, who are generally seem like lunatics to me, I'll be totally honest, like when it comes to this issue. I mean, they seem to literally want to deport 15 or 20 million people and drag them out of the country at an expense of 20, 30, $40,000 each, and people who have kids in schools here who are cleaning bathrooms, picking cherries and washing dishes and just incredible human beings living the American dream. It's just abhorrent and ridiculous and impractical. And you could come up with a million ways to describe how stupid it is, how stupid, cruel, or impractical it is to drag 15 million people that we brought into this country. And when I say we, I mean America, we have to own that fact. Whether it happened under Clinton, Bush, Obama, Trump won, which plenty of people came in under Trump won, or Biden went a lot.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Two information sources. Don't have an example of a founder not getting a green card or into the country. I have heard one or two. I want to bring a developer. I'm trying to bring somebody in from Canada. They're kind of like in the Canadian way station. There should be a little more discussion about this from our friends who are in the administration. I'm not going to say I'm not going to call people out by name. You all know my friends who are in the administration. I think it's a delicate balance inside the party.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Eventually, these private market valuations will run into a public market and a re-underwriting, as my friend Shamath would say, you have to re-underwrite it. And when you re-underwrite it, you know, and Warren Buffett or Bill Ackman or. Pick your public market investor when you get re underwrited, they're going to say, okay, yeah, this is what it's worth. And so, but that's the, you know, no crying in the casino. You're making a bet. We just talked about the previous company, Windsurf, they're making a bet too. So maybe this group had the chance to sell at a crazy valuation and didn't. And uh oh, they should have taken it.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Times their top line sales, four times that equals their market cap. That's called price to sales. So that would be one twentieth of this value.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“If you were to look at what the market's trading at, if you pulled up HubSpot or Palantir, these are two very hot companies that have subscription models. You know, what are they trading at? Those are the two hottest. Palantir has left reality. That's a meme stock. So we'll take that one off the table. But if you were to look at.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“At least a 10% lift. It might be 25% lift per year per developer, a 10% lift on their salary is a market value of $30, $40, $50 billion, maybe $100 billion if it was 20% lift. So then how much of that could the cursor market capture and on the windsurf market? Yeah. Best advice yell off. Go for the gold. And here's the thing these founders go ahead and sell $100 million in secondary each. Tell General Catalyst, tell founders fun they got the money called Brian Singerman. Hey, Brian, I need 50 million. My two co-founders, they need 50 million each. We're going to go buy our net jets cards and our ski houses, and we're done here. Next story.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Trends aren't going to slow down. 40 billion in value, even if you only claim 10 of that, that's 4 billion in revenue. So, what I did here in this back of the envelope calculation is what a lot of, this is what we call bottom-up TAM. We study this in our accelerators, TAM, total addressable market. You could say, what's the market for a co-pilots? And you could say, okay, well, this is the number of pliers. Here's what they're making. They're growing at this percentage. That's one way to make the TAM. What I did was I did a bottom-up TAM of using a different variable. The implied efficiency created per year per developer, how many developers, average salary. So the value creation.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“When you can see very clearly the path to a $10 billion company. And when you see that, like I saw that with Uber and Robinhood, it became pretty clear, like you don't see that with every company. You know, you see, okay, yeah, I could see this getting to $100 million in revenue. I could see this getting to 500 million in revenue, but if they're 16 to, I've heard the number 15 million and 30 million as the number of developers in the world. I'll pick 20 million as just an easy bogey here. You know, these things are going to make each developer 10% more effective and developer being 10% more effective on an average salary of $100,000 globally is $10,000, $10,000 times $2 million would be $10, 2,000 developers at $10,000 per developer is $20 billion. And if you were to... Double that And”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, but you know, general catalyst is like one of these mega multi billion dollar funds This is a great moment to be in in our industry. So many companies are developing powerful new AI apps that are going to radically improve your productivity, but Google has been off to the races. They got a new product. It's called Canvas. And this platform comes with Gemini two point five Pro model baked in. It's Vibe Code Ready, ideal for control freaks like me.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Know who's the investor in this company, like who's on the board and who the investor is, but I guess sometimes getting a quick win is good, but this might be an Instagram YouTube-like situation where in 10 years, this company could be worth $100 billion. So what are we doing here? This is one of the biggest prizes. In AI. I would say, you know, if you were going to pick the top 10 prizes in AI. Robotics and the humanoid robot is one, self driving is one, biology, drug discovery, that whole sort of category is one. This is one if we're going to talk, and probably military applications is another. Yeah, this is one of the biggest prizes.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Windsurf needs to go talk to three other people because I think they can add, I don't know, they might be able to add 3x. This should be a $10 billion deal. I think they're selling way too early. This is a big mistake. Listen, I'm not trying to make the check go up Sam Altman. I'm just saying it's pretty clear based on the reporting and based on what I'm seeing here that this company could do better than $3 billion at this moment in time. This is a big category. What is cursor making in revenue?”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Not fine-alized. Wait, wait. If it's not finalized, I got a piece of advice here. Made an agreement That was a week ago to buy for $3 billion. It's not an open AI had looked at cursor. We knew that. Two days ago, the New York Times reported OpenAI and talks to Acquire Wind That's a big difference. Bloomberg said a week ago that OpenAI reached an agreement to buy winds, sir. Now it's OpenAI is in talks. I'm going to go ahead and advise the team that Windsurf to stop negotiations, leave this deal, raise a billion for Masayoshi San or whoever. UAE, Saudi, Elon. Elon's got a billion dollars.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Buy this thing, we give early access to our developers if they're 1%, they make the company 1% better because of it. Oh my God. So here we go. They're making much faster progress because they are a dedicated team. They probably have a significant earnout for hitting milestones. And this is going to just make open AI, the company go faster, and it's going to make everybody who uses it. So this seems like, yeah, pretty interesting.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“The developers. Let's just say they bought it and they didn't release it and they just used it for internal use only, they would need to make OpenAI 1% more valuable to pay for the cost. And this is when we get into the yum yum land of M&A. We've been talking about the Rath Alina Khan. And I told you there's like a little stuff brewing here. Here's where an acquirer has a thesis. And the thesis can lead to extraordinary outcomes for founders, investors in that company. I just gave a thesis which. You would never think of.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Okay, so Windsur Helps developers write code faster. Agentic means agents. So now they have agents going out and doing things autonomously on behalf of developers and or human beings. And OpenAI bought this because it's an important category, perhaps the most important category in AI because it's the one that has a finite data set. It's going to make the best impact. Developers are expensive and we're in a war with talent. So even the open AI team, if they have access to Winsurf early. The purchase of it for three billion dollars, right, which is one percent of the market cap of open AI right now. If it”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source
“Number one. Pretty good. No, that's a Hugo boss. Let me see that. J Crew. That's like off the rack. Let me The Tom Ford. Yep. They got it.”
2025-05-16 · This Week in Startups · Microsoft Layoffs, Immigration Blunders, & Office Hours with Jeremy Redman of Airfive | E2127 · IDENTIFIED FROM THE TRANSCRIPT · source