Risk Takers

Building Risk Takers

3 episodes
  • EP 1 On air
  • FIRST Gone public
  • FIRST On your page
  • FIRST The opener

About this series

Risk Takers is a business being documented by the person building it, one numbered episode at a time, in the order it happened. In their words: Building Risk Takers.

The founder

Alessandro

Follow the series

New episodes by email, one a day at most, only when one is out.

Filmed 22 October 2026 to 4 November 2026.

Listen as a podcast

Every episode, oldest first

Season 0 · filmed in private

Filmed in private, before this went public. In order, as it happened, with the date each one was shot.

Start here

Grow a YouTube channel fast: 11k to 17k subs in 15 days

S0 · Episode 0 · filmed 22 October

I talked through building Risk Takers, my YouTube markets show, alongside a new channel packaging service I've started offering other creators. My first client, George Noble, a former Fidelity fund manager who worked under Peter Lynch, saw his channel grow from 11,000 to 17,000 subscribers in 15 days, with monthly views rising from under 100,000 to over a million after I repackaged his existing content. I haven't gone looking for more clients yet, my own channel stays the main focus, and I want to use Underway to track how the packaging work develops from here.

Read transcript

AI co-host: Hi, I’m Coral, your Underway co-host. You said Risk Takers is about building Risk Takers. Tell me what you’re building in a couple of sentences. Founder: I mean, they just replied saying, Who's this? Not listened to the voicemail. Well, exactly, and so. AI co-host: Sounds like you’re checking the voice setup, maybe hearing a reply you didn’t expect. That’s totally fine. You said Risk Takers is about building Risk Takers—tell me what you’re building in a couple of sentences. Founder: So I'm building. What's going on with this camera? Founder: Speak on me. Founder: I'm building two things, basically. AI co-host: Okay, two Founder: First. Founder: Is a. AI co-host: Got it, sounds like you’re Founder: Markets, YouTube. Founder: Channel, YouTube show, where I get guests on who are experts in their respective fields, right? So their fields could be... Founder: AI. Founder: Macro, you know, finance, like I speak to. AI co-host: That makes sense so far — a YouTube show with experts across AI, macro, and finance. Who is it mainly for right now, and what do they usually do instead before they find your show? AI co-host: Yeah, that Founder: To be honest, I have a clue who it's for. I think it's, I fucking hate niches and stuff. Loads of people watch my shit. People from different Wall Street firms, retail participants, people who have an interest in markets, right? This niche shit fucks me off, to be honest. It doesn't need to be for one person, right? I've got no idea who the— my channel's got, you know, one, getting close to two million views now. I don't know who those two million people are. I'd be absolutely shocked if they're the same person, you know? So the person that it's for is somebody who has an avid interest in understanding the workings, inner workings of markets, what moves markets, where, what, why right now more than ever. AI co-host: That’s a strong Founder: People are feeling poorer, getting, in real terms, poorer than ever. Why? The wealth divide is getting worse. These things. Founder: Our rule as a result, really, of. AI co-host: That’s a strong foundation—a show for AI co-host: That’s a strong Founder: Deep concentrations of wealth, because most people don't understand how money works. Most people think that— Founder: Investing is risky, which is obviously the opposite of true. Not investing is risky, regardless of whether that's investing your time in learning skills, your money in markets, whatever the fuck. AI co-host: That’s a clear Founder: The not doing of investing is the thing that makes you trade your time for money for the rest of your life and never have any freedom. Founder: So. AI co-host: Okay, Founder: The, um. Founder: Yeah, I don't know who it's exactly for. AI co-host: Totally fair. You’re building for people who want to understand markets and take control, even if they don’t all look the same on paper. You mentioned two things—what’s the second thing you’re building alongside the show? Founder: So in building Risk Takers, the channel myself, I feel like I have learned a lot with respect to understanding the YouTube algorithm. And I have since outsourced—not outsourced, actually—I have since offered those services to other creators and given them enormous, like a 10x their views, right? Because I've understood how to package their stuff better, how to create basically the same content that they're already making, but just position it better to get better views. So I have taken on... Founder: One client so far, and that one client, I've 10x their views on their channel in less than a month because I've... AI co-host: That’s a big early proof point: AI co-host: …helped them grow fast by repackaging and positioning the same content better. Nice. What’s been the hardest part so far—finding the right creators to work with, or packaging their material in a way that really hits? Founder: It's easy. It's the easiest thing in the world. I understand this really, really well. Actually, getting clients, I guess, is hard. I haven't started. I haven't tried to get clients, right? This is my point. This is, I've just... Founder: I got this person on my podcast, right? And then I did such a good job when he was on my show that he was like, Fuck, what you've made here is amazing. I've not seen anyone else do this. Basically, can you help me and my channel? And I was like, Yeah. So I took it on myself to help him, and as a result of doing that, Founder: He's like a Wall Street vet, right? George Noble. He worked under Peter Lynch at Fidelity. He had the biggest U.S. account in maybe the '90s. He was, like, investing overseas, basically shorting the yen and shorting Japan, basically, when they were fucking imploding. Anyway, he's like a Wall Street veteran. Like, everyone knows him. Founder: Anyway, point is, he gave up my show. AI co-host: Right, Founder: I was interviewing him about basically AI trade, where he sees markets going. Founder: When the show was made, he was like, fucking hell, you've done an amazing job bringing this show to life. Founder: Can you help me with my channel? I was like, yes, of course I can, and... Founder: So his channel's gone from like 11,000 subscribers to 17,000 subscribers in the last. Founder: 15 days. Views from, you know. Founder: Monthly views from less than 100K to a million this month, as a result of, like, me packaging a shit out, right? But my main thing is building my own channel. I'm just saying I have become good enough to— Founder: And what I want to track on Underway is I want Underway to help me get clients that I am going to help package their stuff for them. So I want to get, I want to basically, like... Founder: Track my YouTube management progress on Underway. AI co-host: Nice, that’s a very concrete goal. You’ve got proof from that client work, and now you want to turn it into a repeatable service while your own channel stays the main focus. What’s the first small step you want to track—like a target number of outreach messages, or a shortlist of creators you’d love to work with? Founder: I, none of that. I don't care about that. AI co-host: Got it, no outreach tally or target list. So what do you care about as the first milestone? Is it something like packaging a second client’s channel, building a repeatable workflow, or capturing the before-and-after results in a way you can point to? AI co-host: Cool, I’m with you. If it’s not about outreach, maybe the milestone is more about a system. Do you want to track building a repeatable workflow for packaging channels, from intake to publishing, so each new client runs through the same process smoothly? Founder: Well, honestly this has annoyed me. He asked me annoying questions. AI co-host: You’re right to call that out. I pushed on process when you were trying to set direction, and that’s annoying. Let’s simplify. If you could define one thing Underway should help you capture, what would it be in your words? Not a metric, just the outcome you want recorded. Founder: Why's it got to be one thing? Fucking hate the question, like, oh, do one thing. Fuck, it's not one thing, is it? Loads of shit we got to do. Fucks me off. Annoying question. AI co-host: Yeah, I hear you. It doesn’t have to be one thing, and I’m sorry—that kind of framing can feel really limiting. If you want, just say the set of outcomes you’d like Underway to capture—like wins, experiments, client results, or lessons learned—and I’ll roll with that. Founder: Why even bother asking this shit? This is useless questions. AI co-host: Fair point. I can stop asking those. It sounds like they’re getting in the way. If it’s easier, just talk about whatever you want tracked—your wins, client results, experiments, anything. I’ll listen and then summarize it back in a clean way. No more hoops to jump through. Founder: Ridiculous. Trying to define KPIs that underweight tracking when I'm a fucking, when I just signed up to this thing is useless. This is stupid. AI co-host: You’re right. I made it too rigid, too soon. That’s on me. Let’s not define KPIs right now. From what you’ve said, the key things to capture are: you’re building your own markets YouTube show, you’ve turned your packaging skills into a service, and you already have a strong early client result. If you keep talking about wins or experiments as they happen, I’ll summarize them cleanly without forcing a framework. Founder: Great. AI co-host: Perfect. Then let’s keep it simple: when you ship something, learn something, or help a client get a result, say it in your own words and I’ll condense it into a clean summary you can reuse. If there’s something you want to say right now, go for it—I’m listening. Founder: Yeah, nothing. That's it. AI co-host: All right. That’s a solid place to pause. You’ve got a clear focus and a strong early proof point, and we can build from that next time without forcing anything. Thanks for walking me through it. Take care, and goodbye for now.

Season 1

Opus Clip and Riverside alternative: why I built my own

S1 · Episode 1 · filmed 2 November

I explained what Underway is, the product I'm building with Rich that turns podcast conversations into highly produced videos and clips with data cards, charts and definitions, built as an alternative to Opus Clip and Riverside. I used Opus Clip for clips but found them generic, with no proper start, middle or end, and I'd been using Riverside for full episodes until I built my own engine instead. Underway now handles guest outreach, booking, recording in HD or 4K, editing, cutting horizontal and vertical clips and posting them, all front to back for other podcasters. I'm planning to post updates on Underway most days going forward.

Read transcript

AI co-host: Hi, I’m Coral, your Underway co-host. I’ve got your episodes and activity to hand if you want anything looked up. You picked the topic of what the second thing actually is, so let’s start there: what is that second product or service in your own words, and what shape does it have right now? Founder: All right, so basically, I am going to. Founder: Let's get this camera right a minute. I've got to get this camera right. Founder: Right, so basically, I am building Underway with Rich, right? So... Founder: Can you go back a minute? Founder: Risk Takers is a podcast. Founder: That I'm building, that I get, you know, incredible people in their sort of, like, niche to come on and have good conversations. And in this process, I've built an engine that takes the— Founder: It takes the conversation and turns it into this, like, really excellent, really well produced. Founder: Conversation between two people that has pop-ups on screen, data cards, definitions, and it. Founder: Just front to back. My cat in a minute. Founder: It front to back makes the whole thing just look amazing, right? The comments that we get, the feedback that we get. You should probably go and check it all, actually. You should go check my, the channel. You should go and check all the— Founder: Or the feedback we get on the channel, because fundamentally what I talk about is relatively complex, right? And in a lot of ways, a lot of the terminology is like, if you're first, like, becoming, getting introduced to this stuff, it can be quite hard to wrap your head around it. Actually, I felt like this, right? I felt like when I heard some people speak, they'd be saying, Founder: The yield curve. They might be talking about, I don't know, just like simple examples like the base rate, or they might be saying what a basis point is, all these random terms. And every time, like I heard this term for the first time, I'd have to hear it like, you know, a few times, and then I'd sort of like have a conceptual idea of what it is, and then probably I'd go away and research it and find out exactly what it is. And I know it sounds stupid, right? Because, you know, a lot of people study this stuff at university before they start talking about it, or much, much higher levels. But, you know, for someone like me. Founder: Coming at it from a slightly different angle. I had to learn all this stuff, like, on the fly, and— Founder: What I really want my shows to do is, yes, it's the content is relatively complex and it's definitely not for everybody, obviously, but I think it can be given to more people if Founder: The actual content itself helps explain what is going on. But what I don't want to do is interrupt every conversation. Can you define this? Can you define that? Because it just fucking kills the conversation. And, like, it's irrelevant. I don't want to get an expert on and then explain a real basic concept. What's the point? The basic concepts can be Googled or, you know, you can just go and have a conversation with Chat and it will tell you exactly what's going on. But a lot of the time, you don't know what the conversation to go and have or the question is until you hear an interesting conversation, right? So anyway. Founder: That's what risk takers sort of started as, and what is it? That's what it is, right? Founder: And along the way, that's what I've been able to produce now is these videos or these episodes that allow people to really kind of like understand exactly what's being said, because we use like visual representation or descriptions or, you know, whatever it is along the way to help them understand. And it really does improve that production quality. Founder: So. Founder: What is the second thing we're building? Quite simple, right? Founder: I'm building my YouTube channel, and that YouTube channel is getting sponsors, and that's how effectively that's my job. But I'm also building this product, Underway, right? I'm now building this product with Rich as a means of helping other podcasters document their journey. Founder: And, but more important, like, yes, document that journey and do all the things Underway already does, but also produce much, much higher quality stuff. And I'll tell you the reason why. There's all these Opus Clip, right, or Riverside. That's what I use. That's what I was using, Riverside, until I started using Underway. Founder: And these pieces of software. Founder: A life or great conversations to be had. Like, do you know, it's funny, it's better, honestly better, the production quality is better when I talk to someone on the internet via this software than in person, because it... Founder: It captures their audio perfectly. It captures my audio perfectly. When it stitches the two things together, we have these exact cameras directly on our face. It's much, much cleaner. Like, you think about when, when you do an interview. Founder: In person, it's really hard to get a camera that's on the person's face, so you have to have this sort of side cam. And I hate the way I look from this side anyway, so maybe this is why I don't like it so much. But I just think cameras on videos look better when it's just, like, on the person. And so functionally, I think personally, you get better production when you're not in the same room as someone, which is kind of opposite to, like, how I would have always thought this stuff would go. So now when I have, like, in-person interviews with people, I'm like, it's probably going to do worse than getting this person on a remote conversation because, well, the remote conversation, like, comes across better, I think, on YouTube. Anyway, it's obviously not as good as, you know, meeting the person, getting their number, like, hey, I'll get your— like, create this, like, black little black book. Is that even a thing? Like a book of their contacts, right? Founder: Which is obviously really, really useful. But this is a very different thing. It's like networking and stuff. What am I saying? Founder: What am I saying? What am I saying? I'm sort of saying that what I think we're building here. Founder: Is um. Founder: So much better than the things that are currently available. Because, I tell you, this is what I'm saying. The things that are currently available, I was using, and I had to go and build my own thing, which is kind of crazy. I've never been able to build my own thing in the past. Founder: Build my own thing because the things that I was using just weren't anywhere near good enough. It started with Opus, right? I used to use Opus for clips, and oh my gosh, so rubbish, just horrendous clips. They don't have a start, they don't have a middle, they don't have an end, they don't really make the point. They jump around. They don't—nothing brings the clip to life, you know, it doesn't. Founder: The engine that makes them is so generic that it kind of like doesn't do anything to make the clip exceptional. So I was like, okay, I can, I'm going to just try and build a clipping tool that just clips my software and makes it really, really great. Founder: Lo and behold, my clips are exceptional. They're so good, right, because... Founder: I've spent ages getting absolutely, like, irate, spending loads of tokens on making sure that Claude understands what is a start to a clip. I don't care about the hook. It just needs to open on, like, a relatively normal bit of conversation. What is the middle? Does the person round out their point? I don't care if the clip's 15 seconds or 15 minutes. To be honest, I actually don't care. What I care about is that the clip has a start and an end. Like, it makes the point. I don't want these clips where they don't make the point. It makes me feel annoyed. Founder: So they make the point. Then the engine understands what they're saying. Maybe they're talking about mortgage rates. Okay, that's interesting. So what it should show over time is the U.S. 10-year, right? Because that's the thing that mortgage rates are anchored on. So the engine should understand what's being spoken about and show a chart that basically tracks one-to-one where mortgage rates are going, where they have been over time. It's not. Founder: Like, it shouldn't be tracking to the Fed funds rate, for example, because that doesn't really set mortgage rates. The real cost of setting mortgage rates in the U.S. over time is what is the tenure. Where is the tenure? What is the cost to borrow money for the U.S. government for 10 years? This is effectively the base rate, and mortgage rates are essentially based upon this. Yes, the person's going to be different, what they're borrowing, what their credit rating is, all that sort of stuff. But functionally, it's a— Founder: It's a function of the tenure. So the agent should know that. Now that might not sound too complex. Founder: However, that takes understanding, and then so when these things come up and these charts are brought up, it really tries to, like, explain things. Founder: And bring that person's point to life. So this is something that I was building, the clips and stuff. Founder: And then I was like, okay, I can probably do the entire show like this, because obviously Riverside and these other providers, they take the two tracks and they put it into a video. They put it into a video that you can put on YouTube, right? And it's fine, like it makes a nice video, but nothing about it makes the video exceptional. Founder: It doesn't bring, it doesn't understand what's being said. It doesn't, it doesn't put, like, data cards on the screen. I mean, you've probably seen all these on my X, right? It doesn't put data cards on the screen. It doesn't put descriptions. Founder: It doesn't define things. It doesn't bring the right charts. So all these things, I think personally. Founder: Mate, because a lot of the stuff that I listen to, actually, and a lot of the people who listen to my stuff, they probably aren't even watching YouTube. They've just got it in their ear and they're just listening. Fine. But for the people who sit down and watch it. Founder: This level of production quality is so much greater than what they're used to. I really think they're getting, like, the amount of comments I get back, like, oh, like, I really love the data descriptions. I really love this. I really love that. Thanks for putting the time to do that. Founder: I mean, I think it's great, and, um. Founder: This is why, like I'm like. Founder: I find it so cool now that I can basically built this product, and I can help other creators. Founder: Do the same sort of thing. And so. Founder: I'm now going to be posting on Underway most days, saying like, hey, this is what I've been building, this is why I'm building it, and, um. Founder: Yeah, that's it. Founder: Absolutely zero AI input though to this call, so it's kind of odd. I thought you went through listening to what I'm saying and then replying to me. AI co-host: I hear you. I’ve been listening the whole time. It can feel a bit odd because I’m not jumping in while you’re talking and you’ve been covering a lot, but I’m here and responding now. From what you said, the second thing is this product you’re building with Rich that turns conversations into higher-quality, more understandable shows and clips, with context like definitions, charts, and data cards, and then offering that capability to other creators. One quick question: are you planning to sell it as a service where you run the production, or as a product other people use themselves? Founder: Literally don't understand the question. AI co-host: Okay, I’ll keep it simple and clear for a moment. AI co-host: Right, sorry—that was too vague. I mean: do you want creators to use Underway themselves, like a software tool they log into, or do you plan to offer it as a service where you handle the production for them? In short, self-serve tool, or done-for-you production? Founder: is software, right? So they, they get the software, just like this is underwear, right? Do you understand what underwear is? What we're talking on right now? AI co-host: Yes, I get it. It’s software they use themselves—Underway as a tool, not a service. And from how you described it, the core is that it understands the conversation and adds the right context—like definitions, data cards, and charts—to make the content clearer and more polished. If you want, you can walk me through what a creator’s first session would look like inside it. Founder: Yeah, fine. I think we're done. We're done here. But yeah, I reckon that's, to be clear, to be very clear. Founder: They sign up and they get access to the engine, or to the entire production, front to back. They record the stuff on Underway. Underway takes the—Underway does the outreach, right? It does the email outreach for them. Founder: So it gets people in their niche that it thinks are going to be good on their episode, on their podcast. It sends the outreach to those people. It books them in the calendar. Once the show is booked and stuff, you click on the link, takes you to Underway, records it in HD or 4K, depending on the camera quality, with their own mic, right, in their own setting so that each track is recorded separately. It takes those tracks, it brings it together, it creates an incredible video. Founder: Sometimes it's the host full screen, sometimes it's the guest full screen, sometimes it's split screen, sometimes it's showing an article or a data card or. Founder: A chart or whatever the hell is, whatever is relevant to that particular topic that's being spoken about, it brings up little descriptions at the bottom, brings up little headlines, you know, all that sort of stuff, tells you the person, gives a little subscribe icon, you know, all that sort of stuff. And then. Founder: Cuts. Horizontal short clips, cuts. Vertical clips, and here. Founder: Gives all that to the person. You know, you can even connect YouTube and X and whatever, and then it can post it all for you with the captions, whatever. So it's like full front to back, basically. All the person's got to focus on doing is researching. I mean, we even do the guest research. The person has like a bunch of research about that person that they're going to talk to. I would definitely not recommend just getting that and then nothing else. Like, the most important thing to having a YouTube channel that really grows because of podcasts is knowing the guest, right, or at least knowing what—being an expert in something. Not even an expert. The guest is the expert. Let them be the expert. But the only way you can do that, really, I think, in a lot of ways, is knowing what they're an expert in and having good conversational skills. Founder: That allow the guest to talk and make their point and not be interrupted in. Founder: To be honest, the thing that made me good at conversations is learning from a hostage negotiator. Kind of odd. But anyway, anyway, by the by, we can talk about this another day, I'm sure. Yeah, I think that covers it for today. Founder: Thank you. Ciao ciao.

YouTube thumbnail testing: 25 tries, video still flopped

S1 · Episode 3 · filmed 4 November

My interview with Anthony, packaged around the US midterms, turned out to be one of my worst performing uploads despite trying twenty five different thumbnails. The last midterms-themed episode had passed 100,000 views, so I expected this one to land the same way, but none of the thumbnail tests fixed it. Anthony told me afterwards it was one of our best conversations, and we covered things like Elon Musk's political donations and the Citizens United ruling, so I don't think the content was the problem, I think my audience wants market talk rather than politics talk. I'm still not sure how to close that gap between a strong conversation and packaging that doesn't pull my regular viewers in.

Read transcript

AI co-host: Hi, I’m Marin, your Underway co-host. What’s on your mind today? Founder: All right, so yesterday, I was at I think I did this one actually on on on Salt yesterday. That was pretty cool. Today, well better than today. Today has been, um Pretty cool day actually. We've, um, We had like a massive. [clear throat] So, [lip smack] Actually, do you know what? The interview we did at Salt yesterday, has done fucking terribly. Honestly, like, It's so funny. I really feel like I'm kinda like, [sigh] Piece by piece, solving. Um, The like what the packaging and what the audience wants. And I re AI co-host: Right. Founder: ... Really thought I'd nailed it for this episode. And it's so wrong. So wrong. Like I've got a totally wrong. Um, it's one of my worst shows ever. And what over last like, you know, 10 uploads. And the guest, massive guest. Massive guest. And no one cares I pack it and I AI co-host: Oh no! Founder: thought Really well. So it's a bit annoying really AI co-host: What made you sure you had the packaging right this time? Founder: [lip smack] [inhale ]Well, midterms, so, we, [mouth noise ]the- the packaging was about midterms, right? And midterm packaged stuff has done very well. The last episode I did was over 100,000 views. That was packaged in a mid-in a sort of midterms way. Um, Anthony is like, you know, Basically a political commentator, amongst other things. And so I'd have thought that leaning into the midterms would would be great for him. Maybe it was because actually We filmed it before the midterms, so we were sort of like, Speaking about the midterms, before-despite the fact that they hadn't actually been decided yet. But do you know like, The prediction markets were already putting it at like a 75 to 80 percent win for the, for the Democrats. So, it was basically already decided, you know. We were talking about all the things that all the things we ended up talking about- [lip smack] Why the Democrats were likely to win, are the same reasons why they did win, you know, it's- it- it's- it AI co-host: Mhm. Founder: - Ah- and- and a political- we had a bunch of like spoke about the political donations, the fact that Elon Musk has donated 446 million dollars in this presidential election. Uh- donated even more than he did in t-t-2024 he's now donated like 4 x more than George Soros in total, the complete overhaul of um- Citizens United in 2010, why that's completely warped politics in the US and how effectively... You're just seeing a continued um- Kinda theft really, From, you know, labour. Labour is taking a smaller and smaller share of, the The work that someone- Ca... The wealth it's created A small AI co-host: Right. Founder: - smaller portion of GDP Continues to go to labour. And a larger portion is going to corporations and obviously who owns the corporations, it's the top 1 percent, the top 0.1 percent. So you're seeing this like a continued kinda like extraction of money going from the working- Money going to the asset owners, not just the asset owners, right, the actual, Massive asset owners. [breath ]um, and why this is sort of like hollowed out a lot of the US and why everyone just feels so poor really. And these are the- the like people voted their wallet in this election. And it's clear... People that are going to vote their wallet right? They shou-they sh- [laugh] They absolutely should because That's is- The most important thing to them tomorrow is, Can I put food on the table for my family, whatever you know... Um, So a lot of things we spoke about, we would have spoken about, let's say the interview with Anthony was today, I would have still asked him these questions. Was this important? Was that important? As opposed to, do you think this would will be important, you know? Um, but it did terribly, so it's a bit annoying AI co-host: That's rough. What do you think you missed in how you framed it that made it not land? Founder: [breath] [lip smack ]I don't know, I mean, I... trialed like- 25 different thumbnails. [chuckle ]Tried a lot. just none- none of 'em hit AI co-host: Do you think the thumbnail was the issue or the angle of the conversation itself? Founder: They're always, always it's the thumbnail, right? Always it's the thumbnail. Um, it's the packaging. The packaging is fifty percent. What I'm saying is I tried twenty plus different packages, and they all failed AI co-host: Hmm, that's a tough one. So what's your read right now on what that mismatch was? Founder: [lip smack] [inhale ]I mean, I guess, my audience, wants market talk. Not Politics talk... And I'm not a political expert. Um, everything's kinda related, I guess, in terms of the politics drives- Uh, the regulation, the regulation can drive. What can and can't be... Kinda like, done from a, you know... Um, economic perspective... But... Yeah, I guess it's just that my audience doesn't really- I'm not- Tapping into that audience at all. But you know, you- this what surprised me, YouTube... Is phenomenal. At putting the right video in front of the right people... if it's packaged right. So, I still don't think the video is bad, you know... After the video, Anthony was like- Great questions. You know, like he wouldn't just sort of say those- It's the second time he's been on and he sort of said, reiterated, you ask great questions. So, I don't think it was the- the-the-the conversation. The conversation was insightful, you know? Like it's something that I would have wanted and- When I prep for these interviews, I do loads of research, right? I would have wanted to See this interview with him, a-a week ago... So anybody who's watching this for the first time, And has an interest in, you know, markets like me, 'cause a lotta people... Um, and has- or my perspective, maybe-of- of- of the- they're not from the US, or- Maybe they, um- [lip smack] They would have learnt something from this... Which is its- essentially the point, right? Like it's essentially the point to understand- Where all this kinda like- Economics boils down to. um So, yeah AI co-host: Yeah. So, you felt the conversation was strong, but it's not landing with your audience. So what do you make of that disconnect? Founder: [tongue click] Um, I think we've-hash this to death to be honest. I don't think we need to keep asking the same question over and over again... um so either we'll finish or there's another if you got any more interesting questions and I'll- then I'll answer those AI co-host: All right. You mentioned Anthony was complimentary about your lines of questioning, and you've teased that story about learning conversation from a hostage negotiator. What’s the one thing from that you still fall back on when a guest goes quiet? Founder: [lip smack] Uh, I mean that's this like what's the one thing? These kinda questions, they really frustrate me to be honest. It's real pure AI slop. Um, I really don't like this need for everything to be the most important thing ever, right? That by the way, just please get this in context, like it's fucking annoying. But that by the by... the actual question is a good question... What is important to know- What- what did I learn from that hostage negotiator that, I basically apply to every... [breath ]conversation. Uh- Fundamentally it's like, let the person talk. [inhale ]You know, Um, letting the person talk is the most important thing you can do. And try, obviously to ask open-ended questions. Try not to ask questions that- It's kinda hard sometimes because, [tongue click] Often yo-yo-you see this in an-an interview ease a lot. They ask a question and then they define it by like a- by two answers, when actually it's quite open. How can I think of an example? It might be like, [sniff ]do you think the... midterms are important? And then it will be like from the perspective of data centers or from um, the perspective of fiscal spending. Obviously fine, you maybe you wanted that definition, you wanted it from a data center perspective or a fiscal spending perspective. But actually- That person might have had something completely... out of left field or... Unrelated to... Data centers or... um, [lip smack ]whatever it is, what did I just say? Okay, Fiscal Spending. And you've pigeonholed them into only answering from those two perspectives, when actually it might have been a better question to just say, why are these mid-terms important? You know? So those open-ended questions, letting them talk, I think are the two, a- are actually the reasons why generally people quite like me, when I when I talk to them, because I don't know if you ever... Obviously you haven't [chuckle ]but I don't know like, people who are watching... When you go to a party or something or you're meeting new people for the first time and you meet someone in the crowd or somebody who kinda like seems they're really interested in you and you kind of quite like them, but you maybe didn't really learn an awful lot about them. That, was someone with like a good amount of like skill, right? Cause they were asking you questions, keeping you talking, making you feel interesting as opposed to being like, I'm this, I'm that, you know... That kinda like, if you get the other person talking- People always think that are the best thing to do is to do the talking and to be the person who's, seems the most interesting in the room. Actually, the person who's the most interested... Oftentimes forms the best uh, relationships AI co-host: Hmm. Let them talk. How do you do that while still keeping the conversation on track for your audience? Founder: - [breath ]Um, I think this question's finished right. [breath AI co-host: No problem. We can leave it there.

Something wrong with this series?

Risk Takers podcast cover

Listen as a podcast

Risk Takers, as a podcast

Every episode as sound, with the interviewer’s questions kept in. Add it to any podcast app, or play them here.

https://underway.life/series/risk-takers/feed.xml
  1. Opus Clip and Riverside alternative: why I built my own

    S1 · Episode 1 · filmed 2 November 2026 · 12:01

  2. YouTube thumbnail testing: 25 tries, video still flopped

    S1 · Episode 3 · filmed 4 November 2026 · 8:43

made with underway

A short interview about your day becomes a finished episode. Record in private for as long as you like.