86 minutes of paid-UGC alpha | Hector Serrano (Wispr Flow)

1. 0:00 – 1:17

   Teaser

   1. LRLenny Rachitsky0:00

      You have been doing this insanely incredible job growing Wispr Flow over the past couple years. You joined Wispr Flow at 19.

   2. HSHector Serrano0:06

      I looked up creator jobs on LinkedIn. Applied to, like, 200 positions. I found some company called Wispr Flow. I applied, had a call with Tanay, and then I joined. I've never worked in a startup. And I told Tanay, like, I was like, "I want equity in Wispr." And Tanay laughed and was like, "I like you, man."

   3. LRLenny Rachitsky0:21

      There's all this talk about no jobs left for young folks. AI is taking everyone's jobs. Young people are actually much better at this work.

   4. HSHector Serrano0:27

      A 30, 40-year-old founder doesn't understand what an 18-year-old kid who's in these Discord chats, scrolling every day on Instagram and TikTok, they don't understand what's actually working and the best ways to approach these new channels. I think it's a no-brainer to have someone like that on your team.

   5. LRLenny Rachitsky0:41

      You actually had this tweet the other day, "The best marketers are allergic to AI."

   6. HSHector Serrano0:44

      If we go out and start making AI slop ads, it's probably not gonna be received really well. There's so much noise. If you actually focus more on the quality and less on the quantity, it gets so easy to cut through the noise.

   7. LRLenny Rachitsky0:55

      Let's talk about paid-UGC. You're getting influencers, creators to create a pitch basically for Wispr.

   8. HSHector Serrano1:00

      And keep it really open for them to experiment, do whatever they see fit. They're not capped at their earnings. We have creators now that are making, like, $13,000 a month.

   9. LRLenny Rachitsky1:08

      The hardest role to hire for right now is someone like you.

   10. HSHector Serrano1:11

       I think if you just think that looking for someone with the best grades or the best school is gonna get you the best hire, you're in for a rude awakening.

2. 1:17 – 3:10

   What Hector does at Wispr Flow

   1. HSHector Serrano1:17

      [upbeat music]

   2. LRLenny Rachitsky1:21

      Hector, thank you so much for being here, and welcome to the podcast.

   3. HSHector Serrano1:25

      Thank you. Thank you. I'm excited to be on.

   4. LRLenny Rachitsky1:27

      I'm even more excited to have you here. What I'm gonna try to do with this conversation is create a very tactical guide to what is working in growing a B2B SaaS product right now. You have been doing this insanely incredible job growing Wispr Flow over the past couple years. Uh, I saw this stat that revenue at Wispr Flow grew 30X in the past year, which is absurd. Uh, you guys recently raised at something like $2 billion in a very competitive market. Clearly, you've figured something out. You've started to share some of the strategies that you've been deploying on X, and so we're gonna be going deeper into the stuff that you've seen work. First of all, give us kind of a sense of what it is you, you're responsible for at Wispr Flow. What's kind of your, your job there, and what do you work on?

   5. HSHector Serrano2:16

      First of all, I just wanna give a lot of credit to the other members of the team. Like, what I touch at the end of the day is a very small part of the business, um, and that's mainly content as a whole. Um, I'm a content creator myself, and that's how I originally came into Wispr, and that role obviously evolved a lot, and now I'm kind of in charge of our paid UGC program on the actual content side. I'm not on the media buying side of things. And then on top of that, also managing our organic channels for our founder, um, like YouTube and Instagram.

   6. LRLenny Rachitsky2:43

      Okay. Awesome. Something that I've noticed about you, and something that I think is really rare these days, is you're, you're very good at breaking through the noise, both in the content you create, like your tweets recently have just gone crazy viral on Twitter. Everyone's sharing it all over my feeds. So clearly you've figured out how to do that yourself. Also, with the, the ad work that you do, the UGC work that you do, also very effective. So there's a lot that we can all learn from you and what you figured out.

   7. HSHector Serrano3:09

      Thank you. Thank you.

3. 3:10 – 4:25

   The number-one growth lever: product-market fit

   1. LRLenny Rachitsky3:11

      So just kind of zooming out first, talk about the, the growth levers that you have been spending time on. What has been working recently in growing Wispr Flow/can work for other B2B SaaS products?

   2. HSHector Serrano3:23

      I think the first one, and it's maybe a bit corny to say, but I think most importantly, Wispr has grown at the rate it has because of the product. It's all... Everything has been product-led growth since the beginning. I joined at the pre-product stage, and I remember we had a few thousand users early on, and just out of nowhere, it just started catching steam. And, like, six months in, I remember Tanay said it. He was like, "Wow, we really found PMF." Like, it found, like, we struck gold. Um, and then from there, just adding on all these other channels, whether it be organic, paid, everything is just adding more fuel to the fire. And what we found a lot of success with, um, through trial and, and error, doing a bunch of different things, me testing a bunch of channels, other people testing a bunch of channels, is, like, one of the main ones we've landed on now is paid, and we're funneling that with a lot of UGC content. And we have a lot of pillars inside of paid, whether that be UGC video, statics, um, influencers, in-house videos, founder storytelling. But yeah, paid ads as a whole, whether it be through Meta, LinkedIn, YouTube, et cetera, has definitely become one of our main pillars at Wispr, and it's one of the things I'm leading on the content side of things.

4. 4:25 – 8:27

   When to start investing in paid ads

   1. LRLenny Rachitsky4:25

      Awesome. Okay. So let's, let's dive in there. But first, I think to your point, it's really important to say, uh, none of this will really work if your product isn't-

   2. HSHector Serrano4:33

      Exactly

   3. LRLenny Rachitsky4:33

      ... great, if there's not real or organic product-market fit already. Um-

   4. HSHector Serrano4:38

      Yeah

   5. LRLenny Rachitsky4:39

      ... I imagine this can work for a little bit, and then it just fades away-

   6. HSHector Serrano4:42

      Yeah

   7. LRLenny Rachitsky4:42

      ... if the product isn't great. So I guess, is that just, like, step, lesson one? This needs-

   8. HSHector Serrano4:46

      Yeah

   9. LRLenny Rachitsky4:46

      ... to be working on its own with, before you start investing in paid?

   10. HSHector Serrano4:49

       Yeah. E- exactly. I have, like, a lot of founders sometimes reach out or, or come by the office or, or friends, and they're like, "What's the hack?" Like, "How did Wispr grow so fast?" And it's like, no disrespect to other products, but it's like if you're not having that growth early on, um, and you're having to force it a little bit too much, then maybe you have to, like, go back to the drawing board a little bit and, like, rethink how you're actually positioning the product. Is it actually valuable to your users? It-- Why isn't it growing, um, by itself organically? And like, yeah, there's really no hack besides having a good product and then adding more, more levers to pull from.

   11. LRLenny Rachitsky5:19

       So let me ask, when do you think it makes sense to start investing in these inorganic channels?

   12. HSHector Serrano5:24

       Well, I think paid is actually one of the best channels to invest on early on, and I learned this from Matt, who was actually our ex-head of growth at Wispr. Um, he's now at, at Viktor. And a lot of his lessons and lessons that I've learned from him is, like, taking this e-com approach, um, to SaaS, which a lot of companies are, like, scared to turn on the, the paid engine. And what happens when you actually turn on the paid engine is you actually learn a lot faster, like, if the messaging actually resonates with your audience. Are you actually able to convert this cold traffic into users? And, like, at the end of the day, most companies aren't that skilled in organic content because it is something very, like, new. Um, and unless you have, like, really young people on your team who really understand these organic channels really well and know how to package it, know how to make the content, it's really hard to actually get any clear numbers on does your product actually have legs? Do people actually resonate with it? Are you actually able to track these conversions, et cetera? So I think paid makes sense from the get-go. Obviously, like, testing within your, your limits and your budgets that you have. But yeah, if you're able to, like, see, I'm able to turn this cold traffic into paying users, then you kind of have, like, a clear signal there that y- this same messaging or this product will also work on organic if you, like, optimize things a bit more.

   13. LRLenny Rachitsky6:34

       I wanna come back to that, just, like, what that early team may look like, even maybe pre-product market fit. But what's really interesting about what you're sharing here is people... You know, paid has been around for a long time, running ads on Instagram, Facebook, TikTok, all these things. Like, there's nothing new as a platform, and what you're saying here is there's still a lot of alpha and opportunity to grow substantially and do something different in paid.

   14. HSHector Serrano6:56

       Yeah, 100%. And, like, a lot of times people also get scared because they'll say, like, "Oh, I don't wanna turn on the paid engine yet or spend a bunch of money because then we're gonna, like, w- we're gonna reach a point where we, like, oversaturate this market or this ICP." But at the end of the day, it's just, like, getting smarter with how you're, again, positioning the product, and there's always new ways, um, or, like, new messaging, new ICPs you can target, and you won't really reach saturation if you're, like, savvy enough with the angles that you're kind of approaching your content with or the paid that you're appro- or how you're approaching that paid mechanism, I guess.

   15. LRLenny Rachitsky7:27

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5. 8:27 – 13:44

   The paid-UGC strategy and how it developed

   1. LRLenny Rachitsky8:27

      today. Okay. So let's actually... Let's dive into this. So let's talk about paid UGC and paid in general. What's kind of the, the overall strategy that you have employed that has worked so well?

   2. HSHector Serrano8:38

      I, I think it would be kind of good to start maybe from what we learned previously, actually.

   3. LRLenny Rachitsky8:42

      Yeah.

   4. HSHector Serrano8:43

      Um, so where do we go back to? I think this was, like, early 2025. We had an intern named Tobin. Uh, he's a good friend now. I don't know if you've heard of him. He also went pretty viral a while back. Um-

   5. LRLenny Rachitsky8:55

      Mm-hmm

   6. HSHector Serrano8:55

      ... he ended up joining Polymarket. But basically, Tobin came on as an early intern marketing hire. Didn't really have any experience, um, besides some, like, basic UGC. I think he was studying finance and wanted to be a lawyer. And he came in, and Tanay just gave him, like, a budget and was like, "Just throw stuff at the wall, see what sticks." Did a few projects. Nothing really worked. And then he found really good success with organic UGC, and this was also around, like, the Clue era when, like, there wasn't that many people doing it successfully.

   7. LRLenny Rachitsky9:24

      Explain organic UGC. What is that exactly?

   8. HSHector Serrano9:26

      Yeah. So organic UGC is you basically get a bunch of creators in a group. These creators will make videos about your product, and then they will post that on their own Instagram pages or own TikTok pages. So imagine you join Wispr's organic UGC group and you make an account called Lenny Wispr's, and then you just upload your videos into there, and then you get paid based off a CPM metric. So maybe it's like, I don't know, $2 per thousand views, and then it tapers off, like, as you get higher and higher. And yeah, Tobin set that up for us. Um, and I think in, like, two and a half months it was, like, 500 million views, super low CPMs, and it, it worked decently well, but I think it was also early on in the organic UGC phase where everyone was really focused on vanity metrics, and they didn't necessarily lead to a lot of conversions because obviously the type of product that Wispr Flow is as well, it's a bit harder to get to students, to get students to pay for it. So ultimately, we ended up killing the program, which I'm not entirely against organic UGC. It's just making sure that you're not, again, chasing the vanity metrics. And then Tobin did this a lot better at Polymarket, and he, like, cracked the code with, um, organic UGC and, like, not just doing very top-of-funnel, um, concepts. But yeah, organic UGC does work. We just didn't see that much success or the success we wanted at Wispr, and it was also gonna be really hard to find someone, uh, to take Tobin's role after he left. So we were like, "Let's just kill this." And then, again, paid was working relatively well for us, so that kind of brings us to where we're at now, where... I mean, not now, but, like, seven months ago I realized that paid was working really well, and I was the one making all the paid assets. So I was like, what if we apply Tobin's playbook from organic UGC of, like, building this community, building this roster, and paying off performance, and we just apply it to paid, and we maybe make the ads a bit more middle of funnel, maybe a bit more pitching the product. Um, I mean, not even just middle of funnel because you need everything in paid ads, but more just, like, pitching the product straight on instead of just, like, um, screen on text ads. And then I stumbled upon Trybe, which I don't know if you want me, you want me to get into that now? Or-

   9. LRLenny Rachitsky11:26

      Yeah, talk about Trybe, and it's T-R-Y-B-E, right?

   10. HSHector Serrano11:29

       Yes, T-R-Y-B-E.

   11. LRLenny Rachitsky11:31

       Mm-hmm.

   12. HSHector Serrano11:31

       So Lukas Pakter, he's this guy who started Trybe, but before that he actually started SquidHaus, um, which is a clothing brand, and he grew it really fast through TikTok Shop. But there wasn't really a way to do the same thing on Meta, so he made this internal tool where they could run creators' ads and pay them based off performance, and then he basically made it available for everyone, and we were one of the first companies to hop on. And when I saw it I was like, "This is a no-brainer." It's like the TikTok Shop method but for Meta ads. And since SaaS companies aren't able to use TikTok Shop, it's like now they've unlocked this sort of, um- ... this new channel for SaaS companies to be able to run performance-based ads. And yeah, we hopped on there, built out our program. And, I mean, if you fast-forward to now, we're now launching, like, 500 to 600 ads every single month, and it's been a great process. Obviously, that's kinda skipping a lot to where we're at now, but just wanted to kinda give an idea of what we tried, how it worked but also didn't work, and then how we ended up on the performance-based model that we have now for paid UGC.

   13. LRLenny Rachitsky12:30

       Okay. Amazing. We're gonna go much deeper, but just to make sure everyone understands what we're talking about here. So when you talk about organic UGC, it's not free. It's basically you're getting influencers, creators to create a pitch basically for Wispr. You take their video, you put it on your channel, and you pay them per views.

   14. HSHector Serrano12:48

       No. So, so they post it on their channels.

   15. LRLenny Rachitsky12:50

       They post it on their channels.

   16. HSHector Serrano12:51

       Yeah, yeah. So it's a CPM-based... So let's say, again, we bring you into the group, and then it- you make your own channels on TikTok and Instagram, and it'll be, like, Lenny Wisprs or Lenny Talks. It can be anything really, but it... You wouldn't post it on your main Instagram. You'd post it on an alternate, um, and then we would pay you a per- a CPM-based.

   17. LRLenny Rachitsky13:10

       Okay. So the big difference here is instead of CPM-based, which is basically views-based, it's a- they take a percentage of spend or, uh, of GMV or spend.

   18. HSHector Serrano13:20

       Yeah, a percentage of spend or GMV, depending on if you're in SaaS or if you're e-com, something like that.

   19. LRLenny Rachitsky13:26

       Awesome. Okay, cool.

   20. HSHector Serrano13:27

       Yeah.

   21. LRLenny Rachitsky13:27

       So you've shifted to this model. It's basically performance-based, uh, UGC. So just to be very clear about what this, how this works, you find... I think you have something maybe, like, 50 creators right now.

   22. HSHector Serrano13:40

       Yeah. Right now we have 50.

   23. LRLenny Rachitsky13:41

       Okay. And we'll talk about the progression that you recommend-

   24. HSHector Serrano13:43

       Yeah

   25. LRLenny Rachitsky13:43

       ... starting

6. 13:44 – 20:07

   How creator compensation works: percent of ad spend vs. GMV

   1. LRLenny Rachitsky13:44

      with a couple. So you find creators. You- they make a video talking about how awesome Wispr Flow is. You use that video as an ad on Meta and TikTok and other platforms.

   2. HSHector Serrano13:54

      Yes.

   3. LRLenny Rachitsky13:54

      And then they get a cut of how that ad performs.

   4. HSHector Serrano13:57

      Percentage, yeah. Exactly.

   5. LRLenny Rachitsky13:59

      And then you have two kind of approaches to the cut they take. Talk about that.

   6. HSHector Serrano14:03

      Yeah. So obviously, we don't wanna just pay creators just off percentage base, especially early on. Because if you come into the group, you make 30 videos, and you only make 100 bucks off of commission, then it is pretty demoralizing. And a lot of times we see with our best creators, they're our best creators because they've stuck around for the longest and they've understood how the model works. So one thing we actually have included is, is, is, is it's called a smart retainer, and what this is, it's basically like us saying, "Okay, we're gonna back you as a creator, and let's say we're gonna, we're gonna do 25 videos, and we're gonna pay you $1,500. As long as you hit that quota of videos, we'll pay you that money." But, um, depending on how much they earn in commissions, then we might top them up or we might not even add that smart retainer in. So I guess to make it a bit more clear, let's say that you're in our program and you hit the 25 videos, and you only make $500 in commissions. Then we will pay you an additional $1,000 because you hit that quota. But let's say that you also hit that quota and you make $3,000 in commission, then you strictly keep commissions and we don't add any smart retainer. So it's kind of us saying, "As long as you hit these videos and you hit these metrics, we will pay you X amount," and it makes it so that creators that join in the group month one, month two, month three, maybe they're not able to reach over that amount in, uh, strictly commissions, but they're able to make some sort of amount of money so that they actually stay dedicated and keep growing. And then three or four months down the line, you see these creators start to break out and make purely commissions-based, which for me as the guy running the program or if you're a brand owner, that's, like, the best thing because you're paying them pure profit or, or pure off the best-performing videos instead of paying out of pocket. Also, I think some good background is I'm a creator myself. So I found that a lot of companies, and even at Wispr we were doing this sometimes as well, is, like, we would give briefs to these creators to make ads for us, and we would give them this whole sheet where it's like, "Don't say this. Say this. Use these hooks. This is how we want you to talk about the product. This is how you need to sell the product." And it's like when you send a creator a 10-page guideline on how they need to shoot their content, what they need to talk about, you end up removing the creative aspect that creators have. Um, and there's nothing more demotivating than that. And I know as a creator, like, if I have a brand that trusts in me, brings me in for a reason, and just opens the doors for me to create content how I see best fit for the product, you're gonna get better content out of me than if you just put me in this box. So that's one of the main reasons that a lot of the creators wanna work in our group, and we also keep it really tight-knit. So it's like this tight-knit feeling. We bring the best of the best, and then on top of that, we keep it really open for them to experiment, do whatever they see fit. They're all fans of the product. And then on top of that, they're not capped at their earnings. We're not paying them $100 per videos. We're not paying them $50 a video. It's not $1,000 for the month. It's like, it's truly uncapped. If they have really good videos and they put a lot of effort in, we have creators now that are making, like, $13,000 a month, and that's not really possible with other forms of UGC or even influencers. They're making more money than, than full-time influencers, and they might have, like, 1,000, 2,000 followers on, on their own Instagram accounts. But this has just been a way for any creator who's talented to be able to make real, like, money.

   7. LRLenny Rachitsky17:06

      Awesome. And the way you do it is if it's a shopping sort of product, you give them percentage of GMV, and then if it's the B2B SaaS product, you give them percentage of ad spend.

   8. HSHector Serrano17:16

      Yeah. Yeah, espe- especially if you have, like, a freemium product where it's hard to track direct conversion because we also don't wanna get in a place where, I don't know, maybe people are converting off their ads or maybe they're not, maybe they're purchasing, and then we're running those ads and profiting off those ads and they're not getting, like... Like, they're not, they're not getting paid what they're worth. And with a product like Wispr where it's kinda hard to track those attributions or it might take a week or two, it's best if we just keep it at percent of ad spend. But obviously if you're, like, selling, I don't know, a water bottle or a T-shirt and it's, like, really easy to track whether the person came from this ad or that ad and if they purchased or not, um, then it makes more sense to do a percent of GMV.

   9. LRLenny Rachitsky17:49

      So the innovation here that has worked really well is giving the creator a kind of a s- a s- a piece of the action of the success of their ad.

   10. HSHector Serrano17:58

       Exactly.

   11. LRLenny Rachitsky17:59

       Awesome. And then also capping the downside so that they can actually spend time doing this versus being worried that they, they're not gonna make a living.

   12. HSHector Serrano18:06

       Yeah. Exactly, 'cause a lot of the times these creators have to... They end up having to constantly be negotiating with brands or working with new companies, learning new things, and it's like- Not only are these creators all power users, but they get to work with the same company every single month. So just think about, like, the compounding effect of how much better their videos get over time instead of, oh, you're this brand who's running a new-- maybe launching a new feature, and you're like, "Okay, let's scramble to find new creators." And it's like, if you already had that internal group of creators who already know your product and already believe in you, and like, some of my creators understand the product better than me almost, and they come up with ideas I never could have came up with. Um, so if you just have that internal group already, it's so easy that when we launch a new thing, whether it was, like, the Wispr notetaker or all these different features that, that we release, it's so easy for me to just drop it in the Discord and be like, "Hey, guys, let's make a video on this," instead of having to go chase around and find all these different creators and brief them, and then the next month they're gone, and then two months down the line, you have to go find them again. Um, so yeah, it, it just makes for a great experience both on the brand side and, and the creator side.

   13. LRLenny Rachitsky19:04

       And this again comes back to the product itself has to be awesome because it'll be very hard to find creators that love your product if the product isn't awesome.

   14. HSHector Serrano19:11

       Yeah. And i-it, and it's just easy to burn out as well as a creator. Like, if you're talking about something you don't believe in, it can get boring really quick.

   15. LRLenny Rachitsky19:18

       Yeah, it's almost a test of product-market fit. Can you find-

   16. HSHector Serrano19:20

       Yeah

   17. LRLenny Rachitsky19:20

       ... creators that are excited about it consistently?

   18. HSHector Serrano19:22

       Yeah, but concerned.

   19. LRLenny Rachitsky19:23

       Yeah.

   20. HSHector Serrano19:24

       That was, that was honestly-- 'Cause I guess some context as well, I was actually, at Wispr, I was the one making every single ad for, like, a year and a half, so I made hundreds and hundreds and hundreds and hundreds of ads. Um, which I guess that's a testament to how much I, I loved Wispr. I didn't go crazy. Um, and, and yeah.

   21. LRLenny Rachitsky19:41

       Do you think that is actually really important for the person that takes this work to have been the person creating the ads before asking-

   22. HSHector Serrano19:46

       Yes

   23. LRLenny Rachitsky19:46

       ... creators to create the ads?

   24. HSHector Serrano19:47

       A thou- a thousand percent, 'cause it goes back kind of to, to the point I had mentioned earlier where a lot of people who've never worked in content or, or who have never worked with creators end up being the ones briefing them and telling them what to do. And it's like you would never have someone who's not an engineer telling the engineer... Like, I would never go up to the engineering team and be like, "Hey, you guys need to solve this problem like this and do this and this and this." They're gonna be like, "What is

7. 20:07 – 25:03

   The profile of a great modern marketing hire

   1. HSHector Serrano20:07

      this guy telling me?"

   2. LRLenny Rachitsky20:08

      Okay. So let's go down this tangent of to find someone like Hector, what, what are-- what does a profile look like if you were to find a Hector to lead this work at your company?

   3. HSHector Serrano20:20

      This is one of the most interesting conversations I have with a lot of my friends, especially Tobin, like I mentioned earlier, because we both couldn't be more opposite from each other. Like, if you look at both of our resumes lined up next to each other and I ask you to pick one or the other, uh, you probably in your head will think it's pretty clear which one would be the right answer, but at the end of the day, both are the right answer. And like, I had a 2.5 GPA. Tobin had a 4.0. I didn't go to a reach school. Tobin went to Waterloo. I played Division I sports. Tobin didn't. And like, there's all these different things, but at the end of the day, we both ended up being great marketers. But that wasn't really evident if you, like, looked at the face value of our resumes. But I think Wispr has done a really good job of, like, seeing one or two really key things, and also, like, being able to see, okay, is this person a good fit for the, for the culture? Do they seem hardworking? If they have the same values or the same culture as people already at Wispr and, like, I feel like Tanay, Daniel, and the rest of the team are really good at not only spotting early talent and seeing what are those key things to look out for, but also seeing, okay, is this a good person, a good human to have on the team? And I think Tobin and I, obviously might be speaking a bit too much for myself, but I think we, we embody those character traits perfectly. And you might be asking like, "Okay, well, what are the traits I need to look for in a good marketing hire?" And it's like, honestly, it's not that complex. It's like, has this person grown an account, even if it's, like, 10,000 followers? And do they somewhat understand what they're talking about in terms of creator and they've made content? Like, that's how basic it is. Like, as long as they have some experience in building a following, even if it's a small following, it shows you that they understand the consistency it takes to, like, grow a social media following. It shows you that they understand trends and how to make a video and how to edit and how to film, et cetera. And yeah, I think that, like, it comes down to that. Like, do they seem like a hard worker? Are they a good person? And do they have those, like, minimum, like, 10,000, 15,000 followers? And then taking a shot on them. And you can't just bring a young person in and then be like, "Okay," like, "You're not where you, where I want you to be." Like, "You're gone." Like, Tanay and Daniel again, and the whole Wispr team always gives us a lot of time to learn and fail. And I know for a fact for the first seven months at Wispr, I was kind of a, uh, [chuckles] I was kind of all over the place. I mean, I still joke about it with Daniel how, um, there was some hard conversations here and there where you're like, "What's Hector doing?" Um, but yeah, they gave me the freedom to, to keep experimenting, keep trying new things, and it didn't really matter if you failed as long as you're con-consistently, like, learning and getting better and getting better. And like, that's the same for Tobin. Tobin came in, they gave him some money and some time to experiment, and after like two months, he found something that worked and it stuck.

   4. LRLenny Rachitsky22:52

      Okay, this is extremely valuable. There was this tweet the other day that came out of just, like, the hardest role to hire for right now is basically someone like you, someone that can talk about the product, the technical aspects, get people excited, make the product compelling, and you're telling us what this profile looks like. So just to reflect back what you just said, one is evidence that they're very hardworking, uh, evidence they're a good person, that their values and culture kind of aligns with your company. Three, they've actually grown a platform to at least 10,000 followers, and this could be any platform like Instagram, TikTok-

   5. HSHector Serrano23:27

      I, I would say Instagram is probably the highest sign because TikTok is typically like a bit more brain rot content, and like Instagram is like a bit more polished, better packaged, and also the followers you get on there as a platform are just better. So I just think Instagram is probably a higher signal than TikTok. It's pretty easy to grow on TikTok, like posting some brain rot stuff, I would say.

   6. LRLenny Rachitsky23:46

      I see. [chuckles] What about like X and YouTube?

   7. HSHector Serrano23:48

      Uh, YouTube is, is decent, but I would say if you understand a platform like Instagram, you can crack any platform. Um, and yeah, that's my experience. I mean, Instagram and YouTube, I would say if you can, if you can crack Instagram and YouTube, I confident, especially if you're a young individual, you can crack any platform. Like I'd-

   8. LRLenny Rachitsky24:05

      Easy

   9. HSHector Serrano24:06

      ... I'd never posted on X much until like two weeks ago when I went from like 500 followers on X to like 18,000 and I wasn't really used to posting on a text-only platform, but I figured it out after, like, a week. It's like, okay, it's a volume game. You need to keep it short, kind of have your own style, and, like, actually give some value. And, like, that was pretty easy to learn. And I also think if you start on X, it's a bit harder to get into video because video is, like, a whole 'nother beast. Sitting down and filming is, is not an easy thing. I've, I've had some colleagues, like, I've pushed them to start making videos. Um, shout out to Eric. He's our, he's our media buyer. I had him make a video, and yeah, he, he struggled a little bit in his first one, but I think it's good to step out of your comfort zone and, and try to film some videos. But yeah, it's definitely not easy. So I would, I would say yes, Instagram and YouTube.

   10. LRLenny Rachitsky24:50

       That's actually how I discovered you on X, and it's [chuckles] just, like, blown up-

   11. HSHector Serrano24:53

       Yeah

   12. LRLenny Rachitsky24:53

       ... on my entire feed is just Hector videos recently. Uh, so, uh, so I didn't realize you just started posting in two weeks. That's insane.

   13. HSHector Serrano25:01

       Yeah.

   14. LRLenny Rachitsky25:01

       Clearly another sign of how effective

8. 25:03 – 28:22

   The importance of young talent

   1. LRLenny Rachitsky25:03

      you are at this. So s- another kind of, uh, bullet point I wanna double down on there is just this idea of young talent. That's something you talk a lot about, just the value and almost, like, the alpha in hiring young people.

   2. HSHector Serrano25:14

      Yeah. I mean, also going back to the point that you had just mentioned, like how it's the ha- hardest role to hire, I think it's very simple. It just boils down to, like, what I mentioned, like, the two resumes. You... There's, there's no clear path for a good marketer or a good modern marketer who understands socials, and if you, like, look for these, uh, things that you might think are high signal whether it's, like, the best grades, the best school, um, cer- certain majors, like, you're not gonna end up with the marketer that you had en- envisioned. Um, so I think that's why it's hard because there's no real, like, defined path of like, okay, this is how you find the next Tobin or the next Hector or the next X person. So yeah, I, I... Like, my suggestion, if you're trying to find someone similar to me, would be try to not find someone sim- similar to me because you're not gonna find the right person. It's just like, give a shot to some kid who has, like, some crazy background, and the crazier the better, and obviously has some, some proof, um, in the work. But yeah, the, uh, the point that you were asking was the importance of young talent, right? And, like, why that really matters.

   3. LRLenny Rachitsky26:10

      Yeah.

   4. HSHector Serrano26:11

      Um, I think I've seen this example, honestly, in a lot of different industries. I don't know if you've heard of Jimmy Farley, but he's, like-

   5. LRLenny Rachitsky26:17

      Mm-hmm

   6. HSHector Serrano26:17

      ... one of the TikTok shop, like, OG guys. Like, he's, he's been on there, I don't know, since he was, like, 17. Built a huge agency, works with some of the biggest brands, and recently I think his agency got acquired by Physician's Choice for, like, $2 million. And now he's, like, in-house with them and also works with other brands. But I've just seen this kid, like, surround himself... I mean, he's older than me now. But I've seen him surround himself with, like, all these older founders, and all these older founders of these eCom brands are always, like, just talking about how, like, having a Jimmy next to you is, like, so much alpha because a 30, 40-year-old founder doesn't understand what an 18-year-old kid who's in these Discord chats or who's scrolling every day on Instagram and TikTok, they don't understand, like, what's actually working and the best ways to approach these new channels. And if you have young people next to you in whatever industry you are, whether you're in SaaS, you're in eCom, whatever it is, and you just find someone that kinda understands the things that you don't and the early things and you're able to ask questions and learn from them, I think it's, like, a no-brainer to have someone like that on your team. 'Cause, like, even, even if you do your best now to dive into TikTok shop or into Trybe, like, you're still gonna struggle because you're not gonna be able maybe to connect as much with the creators, or you're not gonna understand certain things, and it's just gonna take you a, a, a lot longer time to get used to those things instead of, like, putting your time into something that you're better at and then bringing someone that can kind of manage those things for you.

   7. LRLenny Rachitsky27:37

      I love this advice. There's all this talk about, you know, no, no jobs left for young folks. AI is taking everyone's jobs, and this is a really good example where young people are actually much better at this work.

   8. HSHector Serrano27:47

      Yeah. And I think obviously Tanay is, Tanay is super young, and, like, he's one of the smartest people I know, and, like, he'll still bring me into his office or hop on a call and, like, be asking me like, "Oh, like, what's working on Instagram?" Like, "How are you doing this so fast?" Or, or just, like, ask me questions about content in general, and I don't... I- I mean, I don't think... I've, I've seen this from Tanay and Zahid and the team in general is, like, I don't think there's ever a point where you get smart enough to where you need to stop learning. And if you take that mentality as a founder, I think it's, like, the day you stop growing, and that's something I've definitely learned from Tanay, like, you're never too good or too smart to continue learning, and it can even be from a random 22-year-old or 19-year-old like me.

9. 28:22 – 31:03

   Hector’s journey from D1 soccer to Wispr Flow

   1. HSHector Serrano28:22

      Um-

   2. LRLenny Rachitsky28:22

      Yeah

   3. HSHector Serrano28:22

      ... yeah.

   4. LRLenny Rachitsky28:23

      I love that. And you joined Wispr Flow at 19, right?

   5. HSHector Serrano28:25

      Yes. I had just turned 19. It was, like, three days after my, my birthday.

   6. LRLenny Rachitsky28:29

      [chuckles] Uh-

   7. HSHector Serrano28:31

      Yeah

   8. LRLenny Rachitsky28:31

      ... and how long did it take you to feel like, okay, I've kind of figured something out? You said initially it was kind of rocky and not sure what you were doing.

   9. HSHector Serrano28:37

      Yeah, I mean-

   10. LRLenny Rachitsky28:37

       Just to give people some context.

   11. HSHector Serrano28:38

       It, it was a, it was a weird transition 'cause I had just quit Division 1 soccer, like, three days before as well. Um, and I literally went home, looked up Wispr Flow on LinkedIn. Well, I honestly, I looked up creator jobs on LinkedIn. Um, I applied to, like, 200 positions. I found some company called Wispr Flow. I applied, um, had a call with Tanay, and then I joined. And yeah, it was, it was crazy. Like, s- looking back at some of the memories, like, I remember it was, like, one of the first days when we were getting ready for our launch and I was in my, I think it was my calculus class, and Tanay started Slacking me in class, and I, I left to go to the bathroom and popped up my laptop and I started, um, I hopped into, to the Slack huddle, and he was basically like, "Our launch video isn't what it needs to be. Do you think you can edit it on CapCut or whatever tools you have and make it a bit more Gen Z vibes?" And yeah, I got out of calculus and I just started editing a video. I had some editing experience, but for Tanay, on my, one of my first weeks to ask me to do that was pretty scary. But yeah, that was pretty much summed up my first year at Wispr. I just picked up random stuff. Didn't really have a clear position. I'm pretty sure they didn't really know what I was doing either. I didn't know what I was doing. And yeah, it probably took me a year to, like, feel actually comfortable, and there was, there was a lot of ups and downs. And actually, one thing I want to point out as well is I was also doing a finance internship after... So it'd been a year. It, it had been a whole school year, and then it was my junior year going to senior year, and that summer I had applied... Well, I had applied to a bunch of finance internships early in the year because I didn't know if content was a real career. And, like, obviously I was enjoying Wispr and I was making some decent money for my personal brand But I was like, "I don't know if this is a, a real career." And my parents, like, we immigrated to the US and everything, and like, me being in college and, like, studying finance was a big deal, and they wanted me to go down the traditional route. So I ended up landing a finance internship in New York City, and I was balancing two summer classes, Wispr Flow, and the finance internship. And like, two weeks into the internship, I absolutely hated it and I was like, "I do not want my life to be like this. I need to make content and Wispr work out." So I would sneak out the office and go to some cafes in SoHo and just work on Wispr and my personal content, and then from there, everything started to, like, click. And then, yeah, that, that's kind of how, how it went. [chuckles]

   12. LRLenny Rachitsky30:52

       What a journey. I feel like we could have a whole other conversation about just the creator path and how to become a content creator on Instagram and all these platforms. That's its own, that's its own thing.

   13. HSHector Serrano31:01

       [chuckles]

   14. LRLenny Rachitsky31:02

       I wanna come back

10. 31:03 – 43:03

    Step-by-step: How to build a paid-UGC group from zero

    1. LRLenny Rachitsky31:03

       to how you find the creators for this kind of paid-UGC strategy.

    2. HSHector Serrano31:08

       If we walk through the whole strategy, honestly, now I think this would be a good moment to, to walk through everything. Um, so yeah, like, I guess, like we were mentioning, the first step is kind of figuring out, okay, like if you're in SaaS, you can do percent of ad spend. If you're in e-comm, you can do percent of GMV. And then from there, you'll set up the group in whatever platform you choose. I think Trybe is the best one. It's the one we use at Wispr. And then once you have your group set up, it's like, okay, now you have to go actually find the creators. And if you think about it, it's like, imagine you're starting a company from zero and you land on a platform, and there's thousands of creators, thousands of brands, and your company has no history. More than likely, you're not gonna be able to get the best of the best. Um, and this is where a lot of companies go wrong. They'll start doing a lot of outreach on these platforms, and it's like, why would a creator wanna work for a brand that has, like, no money p- Like, for example, on Trybe, it says how much money we've paid out to creators. It's like $300,000. It says how many creators we have in the group, and then how many ads we have running or whatever. Um, and like, when creators see that we've paid $300,000 out and that we only have 50 creators in, you can imagine the amount of inbound we get. But on the contrary, if you're a brand who has $0 paid out and zero creators, it's gonna be really hard to get creators in. So what I did is I went off platform and I went on platform like Instagram, and you just look up a bunch of keywords. It can be like UGC creators, um, I don't know, tech, nine-to-five, lawyer, doctor, um, sleep, supplements, whatever niche you're in, and just go down a bunch of rabbit holes. And then you'll land on creators that you like, send them a message, and then you also go through their following and follower lists, and you also search those same exact keywords because typically good creators know other good creators. And then I say from around, like, 150 to 250 DMs over a week, and like, these should be very targeted DMs. Like, it shouldn't be like, "Oh, I'm gonna use some mass software and send 3,000 messages." It needs to be very... Y- you need to, you need to care about the small things because nowadays with, like, all these automations, like, yes, you can do a lot of things fast. But if you do it very fast, you're probably gonna get a lot of slop back or a lot of bad creators back. And I, yeah, I think for outreach, it's still better to do it manually. Obviously, it's gonna take a bit longer, but if you do it right, I haven't had to do outreach ever again. Um, and yeah, from those 150 to 250 DMs, you'll probably get, like, five or six really good creators. Then from there, you onboard them to the group, and then that's where you get to the next step, which would be actually building out the culture, um, which is like just doing all these, I guess, events and things for the creators, whether it be like meetings. Um, like we host weekly meetings. Now we're at a stage where we have creator coaches that help keep our creators engaged as well. We do giveaways. Um, we're hosting a retreat in San Francisco next month, um, where we're flying in some of our best creators from around the world. So it's like these little things that you start to do to build up more and more culture. And then from there, so you have a small group of creators. You've also set up the, like, percent of ad spend and percent of GMV, and you've also built a culture. Then from there, you can slowly start to add more and more creators. And the way we did that at Wispr is we probably went from, like, five to 10, 10 to 15, 15 to 20. We probably added, like, five to six creators, like, every few weeks. And since you're now... Since at this point you also have, like, the five creators and you've probably paid out a bit of money, you'll start to get some people start to apply on Trybe. I think now we probably get, like, 1,000 to 1,500 applications a week. So I go through those creator applications, and then from there, since we now have a lot of creators, I keep a really high bar, and I only accept maybe one or two or three. But yeah, we grew pretty slowly, and now we're, like, 50 creators. And aside from, like, accepting creators from Trybe, one other thing we've done actually is we've in- introduced a referral program where we will pay creators $100 per creator they bring in, bring into the group. And it's not some sort of, like, MLM pyramid scheme thing. Like, there was a bunch of people on LinkedIn. My post blew up on LinkedIn, and everyone was like, "This sounds like a scam." Like, "Sounds like a MLM pyramid or whatever, sales." And like, we're not paying them to just bring creators in. It's like we're paying them to send a creator over. If I think they're a good fit, then we'll bring them in. But we don't want more people in. Like, we're capped at 50. It's not like, "Oh, bring me 100 creators and I'll pay you for 100 creators, and then we'll pay another 100 creators." Like, this is a very tight-knit family, and it's just our way of saying thank you for helping us grow the program. And yeah, those are, like, some different levers we've, we've applied to kind of grow the group. And then that brings me to the last step, which I don't know, am I going too fast through this? Or-

    3. LRLenny Rachitsky35:23

       No, keep going. It's great

    4. HSHector Serrano35:23

       ... you probably have some questions you wanna ask after.

    5. LRLenny Rachitsky35:24

       Uh, I do have questions, but keep going.

    6. HSHector Serrano35:26

       Yeah. That brings me to the last step, which is, like, now you have the culture. You have the people in the group. You have... You're at, like, a decent size. You have the, the percent of GMV, percent of ad spend. And now one thing that's gonna start to happen is you're getting a lot of ads, and your ads are gonna show, like, in the group. It's gonna show, like, okay, which is the ad that's getting the most spend, the second most spend, the third spend. And your creators can see these things, and like, obviously you want them to see it, but it can also backfire if you're not, like, good at coaching your creators because these creators will see the top-performing ads and like, they'll be like, "Okay, I want-- I'm gonna copy those ads as well. I'm gonna copy what they're doing." And if you end up doing that, what ends up happening is you get 300 ads that all look the same. They all feel the same. In Meta, when an ad is, like, more than 60% similar, it ends up grouping it together, whether it's, like, the same T-shirts, you're in the same setting, you're saying the same words. Like, Andromeda's super complex now. And for example, it'll scan your ad, like, five times over. It'll pull the transcript. It'll pull, like, each frame out. It'll look at the, the text on screen. And the... If you, like, think about it, like- Like, nothing is gonna get past that. And it, that's why you can reach ad fatigue really quickly if you're constantly repeating the same formats, the same messaging, the same people. Um, so what we do is we continuously, like, push these creators and remind them, like, the reason these creators are making so much money and that their ads are at the top is because they kept experimenting, and they ke- they kept leaning into what they weren't actually good at as creators and what interests them as creators. And if you just follow what person A, B, or C are doing, then your ads are just gonna rank under them, and you're not gonna get any spend. So we constantly push creators to just keep experimenting, keep doing crazy stuff. And when you look at some of the ads in our library, it's like... That's why I say, like, the creators sometimes understand the product better than me and come up with better concepts and ideas better than me, and that's why I stay away from briefs. Like, one example of a really good ad that we had recently was this, this creator had his keyboard outside his window on a roof, and it was raining, and it, it was like, okay, so it's like, it stops you 'cause it's, like, a very interesting visual hook, and then it pans over. Then on the thing it says, "What is my keyboard trying to say?" And it pans over to his laptop, and it's like the raindrops are typing, and then it starts typing random words, and then it says, "Download Wispr Flow." And that ended up becoming one of our best performing ads. And it's like I don't even know how he came up with that, um, so kudos to him. But that's what happens when you keep it really open-ended, you have a fun product, um, and you let the creators have fun and just keep experimenting. And yeah, like, no two ads in our ad library look the same.

    7. LRLenny Rachitsky37:49

       Wow. Amazing. Okay. Let me try to walk through the steps here 'cause this was so much juicy gold stuff, uh, advice. So step one, sign up on Trybe. Trybe is kind of where you manage creators and payout and all that kind of stuff. Uh, your advice here is don't work through Trybe to find them because no one's gonna care about you yet. And your advice is go to Instagram, keyword search for things that are kind of in your market, UGC, tech, lawyers that maybe wanna make money on the side to recruit the first five. The advice is start-

    8. HSHector Serrano38:18

       Exactly

    9. LRLenny Rachitsky38:18

       ... with five. Don't go too big.

    10. HSHector Serrano38:20

        Yeah.

    11. LRLenny Rachitsky38:20

        Okay.

    12. HSHector Serrano38:20

        And I would, I would also... It's not even just start with five or start with lawyers or, or whatever. It's like you have to look at your ad library and look at your product and be like, "Okay, what specific gaps do we have that we actually need to fill in?" Because more isn't necessarily better, and, like, that applies to everything in life. But specifically in creators, if you just bring 100 or 200 of the same creators, that isn't gonna lead to scale because again, everything's gonna look the exact same. But when you bring in five creators that each speak to a specific audience, each speak to maybe a specific messaging of your product, you get five net, five different creators that can all make net new concepts, and, like, it just exponentially grows the more different creators you bring on board. So it's like not just the, the point about bringing a few creators, it's also being very specific about those few creators you're actually bringing in.

    13. LRLenny Rachitsky39:02

        And so when you say that, it's think about what customer or kind of market, what ICP you're targeting, and what's a creator-

    14. HSHector Serrano39:08

        Exactly

    15. LRLenny Rachitsky39:09

        ... that will speak to that audience.

    16. HSHector Serrano39:10

        Exactly. So at Wispr, we have everything from, like, moms to lawyers. We have... Like, the, the awesome thing about Wispr is, like, when you have a product that people love, like, you get so many cool people wanting to work with your brand. We have, like, an eight-figure e-com founder that loves Wispr so much that he just makes ads for us. And it's like, I find that pretty incredible. Like, some dude who has a successful e-com business, he loves Wispr so much that he just wants to be part of the community, and he's like 45, has kids, and yeah. Like, we have basically anything you can imagine, engineers, lawyers, um, moms, uh, sales reps, agency owners, like any, any type of ICP you can imagine. And I get this question a lot as well from a lot of founders in different businesses reaching out, and they'll be like, "Oh, well, I have a dev tool," or, "I'm in the sleep space. I can't make content for, for my brand," or, "I haven't s- had success with UGC." And a lot of the times what happens is people mistake UGC for thinking it's just college kids making content, but UGC is user-generated content, and if you're a dev tool, your user's probably gonna be an older technical person, and you can't get, you can't, you can't get by bringing on 18-year-old who isn't technical to talk about your product, and those ads might look a lot diff- uh, look, they might look a lot different. Like, for example, our technical ads at Wispr, when you're speaking to, like, this older demographic who isn't really on Instagram that much or may- is maybe a bit more serious, the more boring and the uglier the ads are, the better they will perform. And that can be something as simple as, like, a screen recording of someone using your product. It could be like a minute 30 seconds long. It can be super long. Like, some of our best ads, you would look at them, and you would be like, "Holy cow, these are ugly. These are such bad ads." Um, but they actually perform the best for those specific audiences that maybe are a bit older, maybe are a bit more technical. And it's like the same thing for, for a sleep product. Like, if you have an expensive product in the sleep in- sleep niche or industry, whatever, um, and you have an 18-year-old kid selling it, why are you or why am I gonna buy a $3,000 product from a kid? Probably it's not gonna work that way. You wanna buy it from someone who maybe speaks the same way you do, who works in the same things you do, has the same problems you do. Um, and, and yeah, I think UGC works for, for any company. It's just the maybe more upstream you go and the more expensive your product is and the more niche it is, it gets a little bit harder. But it's just like, "Okay, how do I find users who wanna make content about my product?"

    17. LRLenny Rachitsky41:28

        And this unexpected element of what works, um, is part of the reason I imagine you run so many ads. You mentioned you do-

    18. HSHector Serrano41:35

        Exactly

    19. LRLenny Rachitsky41:35

        ... like 700, 500, 1,000 ads a month. Part of the reason is to discover the ones that are working.

    20. HSHector Serrano41:40

        Exactly, yeah. Because a- ads, I would say, is almost weirder than organic content. Like, I can kind of put my finger on what works on organic, but sometimes I'll see an ad that comes in, I'm like, "What the heck is this?" And it ends up becoming the best performer, so that's why I think it's just good to experiment. Don't really have, like, such a high bar for, like, oh, if the ad doesn't look this way or that way, we're not gonna run it. Like, again, some of the ads that I made a year ago, it's literally like a screen recording of someone using the product with some text at the top, 9 by 16, super long video, and they're our best ads, and they're our ugliest [chuckles] ones as well.

    21. LRLenny Rachitsky42:14

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11. 43:03 – 45:37

    Reaching out to creators

    1. LRLenny Rachitsky43:04

       What does the DM look like when you reach out to a creator?

    2. HSHector Serrano43:07

       So it kind of depends, and there's honestly some different ways to go about it. A lot of times, as a brand, you'll actually have a lot of creators already in your DMs or a lot of creators that are already following you. So that's, like, the number one place I would actually start, and a lot of our early creators came from there, is we would just go into our following list and look up UGC or look up creators, and then also go through our DM requests. And you'll actually, like, come across a lot of creators. And from there, it's like they already follow you. They probably already like your product, so it gets really easy, and you can just be like, "Hey, Lenny, I saw your content. I really enjoyed it, and I would love to have you be part of our creator group." And I don't necessarily pitch it... I don't necessarily pitch the performance-based thing yet because it's still a pretty-- it's still a relatively new thing for creators to, like, hear this new model, and a lot of them are skeptical at first, which I understand why. But even, like, seven months ago, six months ago, it was even more, like, new. Um, so even then, like, today, I still wouldn't start with that and, like, go straight into pitching super hard. I'd just be like, "Hey, love your content. Would love to have you be part of our creator group. Are you interested?" From there, you'll get a response back. They'll probably ask you for some more details. And then I have, like, a PDF that's, like, super simple. I just kind of explain the program structure, how much we pay, how much some of our creators are making. And then from there, I'll just hop on a call with them, close them, and get them, like, onboarded in Discord, get them Wispr Flow code, and then get them making videos. And the other way is if they don't follow us and I'm doing outreach is I'll just send them a DM and be like, "Hey, I've stumbled upon across your content. I really enjoyed it. I'd love to have you be part of our Wispr Flow group. This is the tool. This is how it works. Um, here's the link to it. Let me know if you'd be interested." And then from there, if they're interested again, I'll pitch them, and it's kind of the same sort of route.

    3. LRLenny Rachitsky44:45

       And this is from the Wispr Flow Instagram account?

    4. HSHector Serrano44:47

       Sometimes I do either/or because I also-

    5. LRLenny Rachitsky44:49

       Mm-hmm

    6. HSHector Serrano44:49

       ... since I'm a creator myself, I also have a lot of, uh, th- which is also the pros of hiring people who are in content. Some of our best hires at Wispr in content have been through me posting on Instagram Stories or our best creator hires. I'll be like, "Hey, I'm looking for UGC creators. Just post a story." Or, "Hey, I'm looking for a videographer," or, "Hey, I'm looking for an editor." Like, that's one of the cool things about hiring a content creator, um, if, if they make, again, content in y- in your s- niche or they make high-value content is they can also be used as, like, a very good hiring, uh, mechanism. And yeah, it, it depends. Like, if, if you have someone who's a creator, I think it works pretty well. Um, you know, obviously, like, a creator face, whatever. And then also, if you're a really well-known brand, obviously, if your creator getting a message from, like, Nike or whatever, you know what I mean? Like, it, it's very impressive, and you're probably more likely to get

12. 45:37 – 48:31

    Building culture inside your creator group

    1. HSHector Serrano45:37

       a response. So I think it just depends.

    2. LRLenny Rachitsky45:38

       And then, okay, so you DM them. They're interested. You send them kind of an overview. In the early s- say the first five, you said you hop on a call pretty quickly and just kind of pitch them and explain the program. Is c- what's, like, the onboarding look like?

    3. HSHector Serrano45:51

       These creators are very used to just being used and, like, just it's... Everything they do is, like, a transaction. They make a video, they get paid, and they never talk to a person again. And we live in a, like, day and age where everything's digital, everything's virtual. Most people are working remote. Most creators are remote. And they crave community, um, the same way just like a regular person would crave community. And we just make sure, like, that we connect from the get-go and, like, it's like at the end of the day, it's like friends. We're, like, working together. I don't see them as just like, "Hey, a creator that I'm gonna extract some videos from and never talk to again." I get on a call with them, like you said, and have this whole slideshow. But before I go through my slideshow, I, like, ask them about themselves, like, how they got into content, why they enjoy it, and just, like, have a conversation, try to get to know them. And then from there, the flow of the, of the slideshow is I have an intro slide where I talk about myself. I talk about my background as a creator, so, like, they respect me and they know I'm not just some random dude talking to them. Um, and then from there, I'll also intro our media buyer, who's Eric. Shout out to Eric. And then from there, I explain the product. And then from there, I explain how Trybe works. So I, like, I let them know, like, what they can expect in terms of the flow from them making the video to it getting accepted to it getting ran as an ad. I tell them we pay them out every seven days, which is, like, another, um, hack as well. Like, you wanna keep your creators motivated, and the higher the dopamine rush they can get and the more money you can get them early on, the better. Um, so yeah, we pay out seven days. We tell them that. And then from there, we show them some example ads, and then I get them onboarded and fully going on the call. It's almost like you're closing, you're closing, like, a sales deal. You don't wanna get them all excited and then you let them get off, and then you have to chase them down. It's like you wanna be very, um, strategic with your time and their time. So I try to, like, meet them, introduce myself, get them onboarded, and get them going so that they know, like, "Hey, you can start making a video right now."

    4. LRLenny Rachitsky47:41

       So a big lesson here is treat them, treat them like humans. Care about them. Help them feel like they're a part of this thing, not just feel like, "Okay, you're gonna make money. Just shut up. Don't worry about it. You're gonna make money."

    5. HSHector Serrano47:51

       And I think this is actually really good alpha as well is I think the cr- the companies that will win long term are the companies that have the best relationships with creators because words, word gets out really fast. And if you're a brand that treats creators bad, doesn't pay on time, doesn't pay them whatsoever maybe, or you just block them, et cetera, word will get out, and creators probably won't wanna work with you or you won't get the best terms or you won't bet- get the best quality creators. Um, so that's, like, one really big thing we focus on at Wispr. It's, like, not even just with creators, but any external agencies or anyone we work with, we always wanna treat everyone with a lot of respect. Um, and, and yeah, I think, I think it's the companies that do that the best will, will win long term as well.

13. 48:31 – 50:05

    The role of the media buyer alongside the creative lead

    1. LRLenny Rachitsky48:31

       What does the early team look like to start this initiative? Is it just a Hector that is running this solo, or is there a larger team that you'd start with?

    2. HSHector Serrano48:38

       Honestly, it's, it's pretty lean. So our marketing team as a whole is pretty flat. Obviously, we're growing a bit faster now at Wispr. I think we've passed, like, 120 full-time employees now, which is pretty crazy, um, because I joined, I think we were, like, four at the time. I, I remember mes- I messaged Tanay the other day. I was at the office, and I was like, "Holy cow," like, I just had, like, a, a, a moment where I was like, there's so many people around, like, this is crazy, blah, blah, blah. But yeah, right now we're a pretty lean team, and we were even more lean before. But for Trybe specifically, to get something like this running, all you really need is someone like me to kind of be the comms with creators, come up with new concepts, approve videos, kind of get everything kickstarted, and then you need a media buyer. Um, it's pretty rare to find someone who's a creative and also a media buyer. I don't really like numbers that much. I'm not really much of a numbers guy, and I don't like staring at Meta Ads Manager. I've heard it's a headache, um, so I'm happy [chuckles] I don't have to do that. But yeah, we have Eric on the media buying side of things, and he, like, structures our ad account and everything.

    3. LRLenny Rachitsky49:37

       Uh, so when this media buyer, is this kind of like a performance marketing person that just lives in Facebook's ad system, or...?

    4. HSHector Serrano49:44

       Yeah, exactly. So yeah, yeah. Er- Eric's basically just lives in our, on the media buying side of things on Facebook, uh, LinkedIn, YouTube, et cetera. Um-

    5. LRLenny Rachitsky49:54

       Got it. So you're kinda like the creative... You're like the s- the content supply, and then this person-

    6. HSHector Serrano49:59

       Yeah

    7. LRLenny Rachitsky49:59

       ... takes it and then is responsible for running the ads, watching performance, uh-

    8. HSHector Serrano50:03

       Yeah

    9. LRLenny Rachitsky50:03

       ... optimizing the spend.

    10. HSHector Serrano50:04

        Yeah.

14. 50:05 – 53:44

    Team size and structure

    1. LRLenny Rachitsky50:05

       Got it. Okay. And then is there anyone else that you find important, valuable on that team early on and even later on?

    2. HSHector Serrano50:12

       Early, like, if we go back to the early, early days, the marketing team was Daniel, our CMO, um, Matt, who was our head of growth, um, before Eric came, and then it was me just, like, as a sole creator, kind of just making the ads myself. So, and then we had some external agencies here and there, and then slowly we added on design, um, we added on an in-house, like, director to help produce films and launch videos. Um, then we introduced, like, PR recently. And, like, even, even now, I think we're still pretty lean. I think it might be, like, 15 people on the marketing team, like, full time. We have, like, creative partnership leads for, like, influencers. We have a celebrity talent manager who, like, helps us close celebrities and, and things like that. So even then, it's, it's still pretty lean, and everyone is, like, experts in their domain, and it's all very flat. We all just have free reign. We all do what we're best at. There's no real... There's no really middle management. And then poor, our poor CMO, Daniel, who's an absolute legend, he just has a bunch of direct reports. Um, so I feel sorry for his calendar, but yeah, that's, that's kind of how everything is, is structured. It's, like, very flat, no middle managers, and everyone just does their work.

    3. LRLenny Rachitsky51:22

       Is a core kind of takeaway from this conversation that when you're doing paid today, that UGC videos are the way to go versus your own ads that you're just kind of creating?

    4. HSHector Serrano51:34

       So are you kind of comparing to, like, what I was doing versus what we're doing now?

    5. LRLenny Rachitsky51:37

       You know, just like when you think paid ads on Facebook, Instagram, TikTok, most people think, uh, I create a video promoting my product or create, like, an ad unit that is, "Hey, Wispr Flow is the best thing." And what you're doing here is you're having other people create the videos and then running that as the ad.

    6. HSHector Serrano51:52

       Yeah. So the way I look at it is, like, I was basically a u- in-house UGC creator, and it got to a point where ad spend was getting too high, and, like, I'm only human and I couldn't, I couldn't make that many videos, and it was also getting into, like, a year plus of making ads. So naturally, I was getting pretty burnt out being a one-man show and, like, I was like, "Okay, I have the skill set. I'm a decent creator. I can spot, like, good creators as well. Why not just build a team, and that's, like, an extension of myself?" And yeah, that's, that's basically what we did, and we're able to scale a lot faster, test more ideas. Since we have more ad spend, we obviously want more concepts running. And also, like, once you get to a pretty high budget on ads, your ads are typically gonna reach fatigue a lot faster. And especially with Andromeda now, ads reach fatigue even a lot faster, 'cause before, in 2024 when we were running ads, I could have an ad running for 12 months, and that meant my, my output would be a lot less. But now an ad with not only the new updates, but also how much ad spend we're running, an ad, once it hits, like, $100,000 in ad spend, will be dead, and that can be hit in, like, a month or in two weeks, three weeks. So we constantly need more output, more volume, et cetera. And I think that if you look at our ad library, we might have, like, 5,000 lifetime ads and maybe, like, 800 live currently or something like that, or 900 live currently. And it's because, again, they reach fatigue, and then we have to turn them off. But our ad, our ad set or our ad library isn't only full of UGC videos. There's a lot of different things as well. Um, and yeah, everything from, like, statics to, like, high celebrity/influencer videos to in-house ads, to, like, launch videos that we package as ads, to, like, founder-led things. So there's a lot of variety in there, and it's just, just basically h- h- I even, I guess just having as many formats as possible because, again, we have a lot of ad spend, and we want the more variety, the better at

15. 53:44 – 56:15

    Why UGC works even in technical and enterprise SaaS

    1. HSHector Serrano53:44

       the end of the day.

    2. LRLenny Rachitsky53:45

       Okay. So this is just a, a core leg, uh, uh, to the stool of paid ads is UGC, uh-

    3. HSHector Serrano53:51

       Exactly

    4. LRLenny Rachitsky53:51

       ... clearly working. Do you think this will work for every company? Is this something most B2B sa-

    5. HSHector Serrano53:56

       Yeah.

    6. LRLenny Rachitsky53:56

       I don't know. Yeah. Does this... Do you think this won't work?

    7. HSHector Serrano53:57

       Yeah, I think, I th- I think this works for everyone. It's like it goes back to what I was saying, it's just finding those users that can speak to the users you wanna acquire. And at the end of the day, one thing that we look at at Wispr is, like, the B2B side and the enterprise side is all made up of individuals, and if you can find a way to make your content speak to an individual who is part of those teams, and maybe you get them as, like, a solo, how do you say it, like a solo customer or whatever, um, to download the app, they use it, then they tell a friend in the company, and then more people in the company start using it. And then maybe you chase down those enterprise clients and actually close the deal. And, like, that's realistically how most companies can approach that at the end of the day, and it's not like, oh, like, who from X company's gonna watch my video and, like, hop on an enterprise call and, like, wanna close or whatever. But I think if you, like, approach it from, like, companies are made up of people, and you just look at it like that, and you think, "Okay, how, how do I wanna sell to these people, and how would these people respond well to getting sold to?" Um, I think you just have to break it down super simply, and you're like, "Oh, yeah, this would work for anyone."

    8. LRLenny Rachitsky54:57

       Okay. That makes sense. Uh, also what I'm hearing, though, is it's probably most effective for kind of product-led growth, bottom-up sort of products, not like a Workday or a Salesforce.

    9. HSHector Serrano55:07

       Yes.

    10. LRLenny Rachitsky55:07

        More like a, yeah, Wispr Flow or-

    11. HSHector Serrano55:09

        Yeah

    12. LRLenny Rachitsky55:09

        ... Notion and-

    13. HSHector Serrano55:10

        Yeah, exactly

    14. LRLenny Rachitsky55:10

        ... Dremio and things like that. Awesome. And, you know, like, if you think about it, it makes so much sense why this would work. An influencer innately is someone that influences you to do something. You're basically getting influencers/creators to create content that pitches the product, and then you put them in people's feed through paid ads. And I get why it works, 'cause they're-

    15. HSHector Serrano55:30

        Yeah

    16. LRLenny Rachitsky55:30

        ... trying to convince them how awesome it is.

    17. HSHector Serrano55:31

        I, I also, I also think that y- a good distinction as well is, like, it's not just an influencer or a creator. I almost think that creators with no following end up being better investments for brands, because influencers kind of are seen now as sellouts a lot of the time. And, like, when you see a big face or a big celebrity, like, selling a product, it's like, "Oh my gosh, this person has been selling me things for, like, the last 10 years. I know she's just getting a bag," or, "He's just getting a bag." And they're not really genuine, and there's something about, like, not really knowing who the person is, and they're not famous. They don't have a lot of followers. And if you have, like, these partnership ads coming from their account, it just feels a lot more genuine as well, so just wanted to throw that out.

    18. LRLenny Rachitsky56:07

        That makes sense. Like, the less they look like an influencer [chuckles]

    19. HSHector Serrano56:09

        Exactly. Yeah.

    20. LRLenny Rachitsky56:10

        The less they look like they're trying to convince you, and they're just talking like a regular human about-

    21. HSHector Serrano56:13

        Exactly

    22. LRLenny Rachitsky56:14

        ... how awesome your product is,

16. 56:15 – 59:50

    Advice for people embarking on the creator path

    1. LRLenny Rachitsky56:15

       I get why that would work.

    2. HSHector Serrano56:17

       Mm-hmm.

    3. LRLenny Rachitsky56:17

       Like, what I think about right now is there's that survey that they [chuckles] someone did a while ago of just, "So what do you wanna be when you grow up?" And for young people, it was like creator, influencer versus like-

    4. HSHector Serrano56:26

       Yeah, stream. I think a lot of people were saying they wanna be a streamer, a live streamer.

    5. LRLenny Rachitsky56:29

       Streamer.

    6. HSHector Serrano56:29

       Like, like stream-

    7. LRLenny Rachitsky56:30

       Yeah, versus, like, astronaut or lawyer.

    8. HSHector Serrano56:32

       Yeah.

    9. LRLenny Rachitsky56:32

       And so, you know, like, this is a career path is what you're describing. This is a way, you're making money doing this. A lot of people are actually making money being-

    10. HSHector Serrano56:39

        Yeah

    11. LRLenny Rachitsky56:39

        ... a creator online. So s- for people listening that are like, "Wait, maybe this could be a career for me someday. Maybe I should explore this creator life," any advice for someone that's embarking on this? Because for many people, it may feel like, "I will never be as great as Hector at just talking off the cuff on a video and looking interesting." Any advice for someone that's trying to explore this path and do better?

    12. HSHector Serrano57:00

        I think the best advice would be to stop looking for advice. [chuckles] It's, it sounds, it sounds dumb, but a lot of times I'll have a lot of friends reach out, and they're like, "Hey, I wanna get started." And I've had this happen for, like, maybe the last three years where people are like, "Hey, I wanna get started, and I wanna start making videos like you." And I hop on a call with them for, like, two hours. I send them over a bunch of different guides, PDFs, things I've made, et cetera, for how they can get started, and they don't do anything with it. And it's like, at the end of the day, if, if you're a person who's gonna ask before doing, you're probably not gonna succeed, and even the best people... I've, I've had the privilege of working with a lot of the most famous podcasters or influencers or celebrities, and a lot of these people also stutter, and they also have to refilm things. And they have, like, specific things that they do to, like, lock back in, whether it's, like, weird noises they make with their mouth, or, like, they fidget with their hands, or they have, like, a phrase they repeat over and over again. Or I've e- even seen some creators where they start stuttering a lot after they've been doing, um, the same script over and over again, and they'll put a pen in their mouth and will, like, open their mouth bigger and, like, talk and announce, enunciate. Is that how you say it, enunciate the words?

    13. LRLenny Rachitsky58:03

        Mm-hmm.

    14. HSHector Serrano58:03

        Um, like, I guess more, and then when they stop and they take the pen out of their mouth, then they're able to pronounce it better. So it's like, it's, like, a, a natural thing as a creator. And, like, even if you're doing this for five, 10, 15 years, there's gonna be moments where you have to cut the video, or you're gonna stutter and you're gonna have to refilm for 10 times, and you might cuss out your camera and turn it off. But it's just like, turn it back on and keep filming sort of thing. And, and yeah, that'd be my advice. Just get started, um, and stop looking for, for more advice. There's no better way to learn as a creator than, than just turning on the camera and posting.

    15. LRLenny Rachitsky58:34

        I love that advice. And what I'm also hearing is you don't have to... Like, one, you don't see how much people struggle doing this stuff. Like, you see this polished video, and you don't know they had to put a pen in their mouth for-

    16. HSHector Serrano58:45

        Yeah, exactly

    17. LRLenny Rachitsky58:45

        ... a few minutes first.

    18. HSHector Serrano58:46

        Or cuss out their camera. [chuckles]

    19. LRLenny Rachitsky58:47

        Yeah.

    20. HSHector Serrano58:49

        Um, like, e- even, even my video that w- that went kind of viral on X, like, I think it's, what, a 15-minute cut? It was probably, I did two cuts before that, that were probably each, like, 30 minutes. And then I did that last one, which was probably, again, like, 30 minutes, and then I packaged it into a nice video. And it's like, I do this for a living, and I've managed our Trybe group for the last seven months, and I know it like the, like the back of my hand or whatever, and even then I still struggle, like, going through and putting my thoughts concisely and going through everything. But it's not perfect, but I put the message out. I gave some value, and people enjoyed it. And yeah, I don't think, I don't think it needs to be perfect.

    21. LRLenny Rachitsky59:26

        That's so great to hear, 'cause watching that video, you're just so chill, so relaxed, just sitting there talking with a little iPad. And, like-

    22. HSHector Serrano59:32

        Mm-hmm

    23. LRLenny Rachitsky59:32

        ... how, yeah, people see that are like, "I will never be as good at this."

    24. HSHector Serrano59:35

        Yeah.

    25. LRLenny Rachitsky59:35

        So that's really helpful to hear. When I think about starting to create a, be a content creator, I feel like I need to get a little fuzzy mic or something. I feel like the step one-

    26. HSHector Serrano59:42

        It, it, yeah

    27. LRLenny Rachitsky59:43

        ... or a tiny little iPhone.

    28. HSHector Serrano59:44

        It's a canon even- it's a canon event. [chuckles]

    29. LRLenny Rachitsky59:46

        That's right. You're not a creator unless you have a tiny, fuzzy little mic.

    30. HSHector Serrano59:49

        Yeah.
17. 59:50 – 1:02:21

    Common mistakes to avoid

    1. LRLenny Rachitsky59:50

       let me ask you one final question along these lines. Say someone is like, "Amazing, I'm gonna do this. We're gonna commit to this. We're gonna hire. We're gonna find someone to run it." What are some of the most common mistakes you find companies, people make when they're starting on this paid UGC route?

    2. HSHector Serrano1:00:05

       I think a lot of the times is people will typically look in the wrong places, and will maybe put out offers online or on LinkedIn or whatever with too high of salaries or too high, like, I guess, like, requirements, and you're not gonna end up attracting the best people. Like, if you put out an offer where you're gonna pay, I don't know, be like, "Oh, these people who are running UGC campaigns are in super high demand. I'm gonna put out a job listing for 250K, 200K base salary, uh, generous equity," you're gonna end up attracting the wrong type of people. Um, like, when I joined Wispr and when Tobin joined Wispr, I can tell you we were nowhere [chuckles] nowhere near that. Um, we were interns, and we were just hungry kids who wanted to learn and wanted to grow and, again, had some experience with content. And I think if you just think that throwing money out there and looking for someone with the best grades or the best school or the best experience is gonna get you the best hire to run this for you, you're in for a rude awakening. Um, and yeah, I would focus on just finding a scrappy kid who's hungry and willing to learn and, like, I don't know, you just get a good feeling from them. Like, yeah, I, I was talking to Tanay recently as well the other day. Our first call... So I had a first call with Julia, which she was, like, leading our marketing team initially, one of those, like, four people. And then I had a second call with Tanay, and I remember, like, mind you, they're hiring me as a UGC creator. I'm 19 years old. I've never worked in a startup, and I've probably... I was not earning much money, and I told Tanay, like, I was like, "I want equity in Wispr." And Tanay laughed and was like, "I like you, man." And, like, maybe it was, like, a stupid thing to say, but, like, I think it showed how, like, I don't know, I was naive but also hungry, and, like, I believed in the company and I wanted to be part of the company. And just, like, cues like that where it's, like, a young, naive, hungry kid, um, who just wants in and wants to learn and wants to grow and, and yeah, I think don't look in the right place. Don't want- Don't, don't look in the wrong places 'cause you're gonna attract the wrong people.

    3. LRLenny Rachitsky1:01:58

       You had a couple awesome tweets along these lines. One is that everyone looking for a marketer with the best resume is gonna end up hiring a bot.

    4. HSHector Serrano1:02:05

       Yeah. [laughs]

    5. LRLenny Rachitsky1:02:07

       [laughs] And then the other is this really important tweet that the most successful founders, investors, creators I've met aren't the most talented. They're delusionally confident, they outwork everyone, and they love what they do.

    6. HSHector Serrano1:02:18

       Yeah. I think that pretty much sums it up.

18. 1:02:21 – 1:03:52

    The sports approach to hiring

    1. HSHector Serrano1:02:21

       Then also another one that I, that I resonate with a lot that I, that I put out recently was, like, the, the sports outlook on hiring. Sports teams, like, I come from a very competitive sports background. I played over in Spain. I played for Real Madrid Go in La Liga Academy. I played the MLS NEXT in the US. I played Division I in college. And, like, we have all these structures for sports teams where it's like you scout young talent, you bring them in, you coach them, you develop them for 10 years. And then, like, if you're over in Spain or over in Europe, um, you eventually, like, get them as part of your academy, maybe the second team, and then maybe you sell them to a top club. Or maybe they end up becoming a homegrown contract or, and they join, like, your first team. And it's like I think a lot of startups should kind of a- adopt that mentality. Now, um, I think there's a lot of companies that actually don't do internship programs anymore. They don't think they're valuable. And I think they're one of the most valuable things, and if you can find the right people, it's not a very expensive thing to do. It's not very time-consuming. Um, and yeah, I think, like, taking a, a, a chance on young, on young people and giving them some money to, to test things with and giving them some freedom to test things with, um, and, like, allowing them to fail and continue learning is, like, one of the best models I think you can pick up from sports. And, like, obviously it works. Like, I, I don't know if you're very familiar with soccer, but I mean, like, look at Lamine Yamal, like, just won the World Cup at, what, 19 years old, 18 years old. And, like, I think that same approach can be applied to, to the startup world. Like, find young talent, invest in them, let them get real reps in the real world, and then eventually they'll might become one of your A players.

    2. LRLenny Rachitsky1:03:47

       I love that. Uh, and I love that also part of this is giving them time to figure it out.

    3. HSHector Serrano1:03:51

       Yeah.

19. 1:03:52 – 1:08:07

    Why the best marketers are allergic to AI output

    1. HSHector Serrano1:03:53

       100%.

    2. LRLenny Rachitsky1:03:53

       What's really interesting about this conversation so far I'm realizing is I don't think we've once mentioned AI-

    3. HSHector Serrano1:03:58

       [laughs]

    4. LRLenny Rachitsky1:03:58

       ... as part of this work that you do, which is really interesting because it's, you know, it's, it's all anyone talks about these days. And you actually had this tweet the other day, the best marketers are allergic to AI. Talk about just what you th- what you think with how AI plays into this and how AI should not play into this.

    5. HSHector Serrano1:04:15

       I just think, like, overall when you look at a lot of the work done, like, even, like, looking at the top labs, like, they are some of the people that have the most amount of humans actually working on a specific asset and, like, maybe, yes, they have a lot of the research automated or a lot of different steps, like, internally automated, but the actual production of the asset, whether it comes to the video, the design in Figma, um, the editing, the post-production, et cetera, it's all done by teams of a lot of humans. And I think there's not gonna be a real way to get around that, at least not anytime soon. And especially in, like, the environment we're in now where a lot of people are very, I guess, turned off by AI, and it can be s- a scary, like, thing to talk about. If you're an AI company like Wispr, who in theory we enable humans to do better work, we don't want to replace anyone's job. We want to give them, I guess, the tools to be able to be more productive, to do more work, and to sound more naturally, and to sound like themselves more naturally. If we, on the other side, go out and start making AI slop ads and videos with AI influencers and, I don't know, AI designs and AI statics, it's probably not gonna be received really well, and it just, it looks off. And, like, when I say that, I think it goes more towards not automating the work that's gonna be the final product that people are looking at, um, because I think you see a lot of times, like, it'll, it'll end up blowing back on, on the companies, whe- whether it's, like, an animation that they made with Claude or, um, some sort of asset that they made and maybe there's typos or maybe the writing is, like, all jumbled up, like what happens when you do it with, with Open... with ChatGPT or whatever. Um, and yeah, I think it's, it's not worth it. Like, the risk versus reward is not worth it.

    6. LRLenny Rachitsky1:05:55

       So the alpha, what I'm hearing here is, like, don't use AI for this work.

    7. HSHector Serrano1:06:00

       Yeah. For, for the final output, especially on the creative side. Like, what other people are gonna see, I, I don't think AI should, should touch yet. Uh-

    8. LRLenny Rachitsky1:06:07

       That is really interesting. Like, you know-

    9. HSHector Serrano1:06:09

       Yeah

    10. LRLenny Rachitsky1:06:09

        ... people, it feels like everyone's hearing lean into AI. Uh-

    11. HSHector Serrano1:06:12

        Yeah

    12. LRLenny Rachitsky1:06:12

        ... use AI to create launch videos, all these things.

    13. HSHector Serrano1:06:13

        Even, uh, even one of the most bullish people on AI that I know, um, Matt, who is now at, at, at Victor or at Set of Growth, he has the most automations I've ever seen in the whole wide world, but even then, like, that last, um, like, 10% that's the most important always has a human on the endpoint because you can't sacrifice as a brand having something blow up because you had something screw up or come out wrong or, or whatever. And yeah, I think with everyone, I think with everyone also just shipping so much volume and, like, whether it be on X, on LinkedIn, on Instagram, on YouTube, like, you're able now to make videos with Claude. You're able to, to have the, edited them. You're able to make, um, what's it called? It would make like a doppelganger of yourself with AI and, and all these different things, and get content out faster, and have these automations for tweets, and have it, like, post news articles and whatever, and retweet it in whatever way. There's so much noise, like you're saying, that if you actually focus more on the quality and less on the quantity, and less on building all these crazy automations, and hitting volume for just hitting volume's sake, it gets so easy to cut through the noise. And, like, if you actually have real value, you package it well, and you post, like, not a lot, you post with, with purpose and for actual reason, um, you can cut through really easily as a brand or as a company. I, I think another good example of this is also Tanay's YouTube channel. We started it around, like, what? Three months ago, and five YouTube videos in, we're, like, millions and millions of views, 20,000 or 21,000 subscribers on YouTube, which is one of the hardest platforms to grow. And, like, a lot of people think, "Oh, y- we're starting a YouTube channel. We need to post three videos a week." And it's like, no. Like, if you actually put in the time and effort, and you tell a really good story, and you do everything with purpose, and you package it really well, and you have a really good team of humans actually touching everything in there, um, you get really good end product, and people actually can see

20. 1:08:07 – 1:16:01

    Founder-led content

    1. HSHector Serrano1:08:07

       the effort you put into it.

    2. LRLenny Rachitsky1:08:08

       That's actually where I was gonna go, and this could be our final thread to chat through, is just this, uh, other lever, which is, I don't know if you describe as founder-led growth or-

    3. HSHector Serrano1:08:17

       Yeah, founder-led content

    4. LRLenny Rachitsky1:08:18

       ... organics. Founder-led content. Just give us kind of a sense of that growth opportunity, what you're seeing there, the opportunity to drive growth for your product through founder-led content.

    5. HSHector Serrano1:08:28

       Yeah. I think, I think it also ties into what we were just talking about, like, so much AI and so much ads in companies, et cetera. And at the end of the day, it also g- it ties back to everything in content creator and people. Like, at the end of the day, people buy from people, people invest in people. And I think having a founder who can put his face out there, can talk on camera, you can use in ads, you can use to tell the story, it makes the company and the product feel that much more human. And, like, when you compare two products, um, I would much rather, like, even from my own experience, like, if I follow, um, I don't know, let's say I follow George Heaton, who's the founder of Represent, he has, like, a clothing brand, and then there's another ad that I see for a clothing brand, I'm much more gonna buy the product, George's product, because I know how he works. I know his routine. I know the type of person he is. I know what he stands for. Um, I know how hard he works, um, for his company and what he actually puts into it, and I think people really appreciate that. And again, such a digital age, like, being able to connect with the founder behind the product. And you not only, like, create super fans and, like, people who already use your product but now also love you, you also bring in, like, this new group of people who have never seen your product, they don't really know who you are, and then slowly they start to, like, like the content you're putting out. They start to buy into the mission. They start to buy into the company. And then they actually try the product. And it's, like, this long, like, horizon-type play, um, or this, like, long-term play that you have to make. And it's an investment because you can't just start a YouTube channel or founder-led brand and instantly start selling at people because people are just gonna switch off and be like, "Okay, I don't wanna be part of this anymore." But if you just give a lot of value, you overshare, you overdeliver, and you just open up the doors into, like, what the culture's like, what you're building, people really appreciate that, and you get them to buy in and, like, drop their guards. And then maybe a year in, we actually, like, maybe have, like, a soft sell or maybe we have, Tanay have, like, "Hey, guys, here's, like, some support. Thanks for getting us to 100,000 subscribers. Just wanna drop this code," blah, blah, blah, and then people are actually willing to support you. Um, so I think, again, like, in this world where everyone's just trying to get, like, instant growth and everything's super fast and optimize everything from the start, these, like, channels that maybe don't have any direct correlations in the present moment end up being some of the best long-term plays and also brand-building plays.

    6. LRLenny Rachitsky1:10:39

       What are some of the kind of angles/stories that seem to work well when you're doing this sort of founder-led content? Is it, like, here's the story of our company?

    7. HSHector Serrano1:10:47

       Yeah.

    8. LRLenny Rachitsky1:10:47

       Is there anything there?

    9. HSHector Serrano1:10:48

       So the, the way we kind of thought about it at Wispr is it's like... At Wispr, or honestly at any company you're at, is, like, every company is gonna have some sort of story or some sort of mission that they're building towards. For us at Wispr, it's getting to one bi- one billion daily active users, and that's, like, everything. Everything we do at Wispr is to get towards that goal. And when we look at the content we make, everything needs to play back into that story, and it's almost like you're building this Netflix series where each episode is obviously gonna be different, but it all ties back into the overarching theme. And, like, whether you're, again, building in, uh, medicine or, um, dev tools or whatever it is, there's gonna be some sort of mission that you're chasing as a company, and you wanna bring people along for that ride. And if you tie that into every episode or to every LinkedIn post, every X post, um, obviously, like, the formatting and the messaging is different on every platform, but if you, like, kind of tie all of this together, like, brings everyone along for, for the journey, and it makes it a lot easier to grasp, and also a lot easier to build off of because you're like, "Okay, this is the, the vision, this is what we're building towards, and this is how each step actually leads us to that, to that mission." It's almost like a physical representation of, like, a product roadmap or what's actually happening to the company, like, showing it on, on display to the world, the ups, the downs, the struggles, everything. That's kind of how we think about it at, at Wispr and how I think other companies can think about it as well.

    10. LRLenny Rachitsky1:12:04

        That's awesome advice. Basically have, like, a-

    11. HSHector Serrano1:12:07

        A north star. Like a north star metric that you're chasing.

    12. LRLenny Rachitsky1:12:09

        Yeah, and the journey there, and things you're learning-

    13. HSHector Serrano1:12:11

        Yeah, exactly

    14. LRLenny Rachitsky1:12:11

        ... things you're discovering, things that are surprising. And we'll point people to the channel to give them a sense of what you're actually doing there.

    15. HSHector Serrano1:12:16

        Yeah, it's just, uh, Tanay Kothari, and yeah-

    16. LRLenny Rachitsky1:12:19

        Cool

    17. HSHector Serrano1:12:19

        ... we just document everything on there. Like, the episodes, like, we, we've basically done everything from, like, showing how we launched our new product Notetaker to Tanay going to India and doing wedding shopping and, like, also working remote and how he balances that and his relationship with Sahej, um, to, like, just a week in the life of a founder. Uh, uh, we also did a whiteboard breakdown where I spoke with Tanay, and it's, like, all these different formats that all might feel different and look different, but they end up, like, building towards this, like, bigger vision of what Wispr is building towards.

    18. LRLenny Rachitsky1:12:46

        I imagine there's already some innate interest in Wispr Flow by when you started it. It's, like, a company people, when they see it-

    19. HSHector Serrano1:12:52

        Exactly

    20. LRLenny Rachitsky1:12:53

        ... they're like, "Oh, I wanna..."

    21. HSHector Serrano1:12:53

        Yeah.

    22. LRLenny Rachitsky1:12:53

        So there's probably a bit of, like, you can't start that from the beginning when no one cares about what the he-

    23. HSHector Serrano1:12:58

        Yeah

    24. LRLenny Rachitsky1:12:58

        ... no one cares what you've learned 'cause no one cares about your company yet.

    25. HSHector Serrano1:13:00

        Um, I, I honestly think you can start it though.

    26. LRLenny Rachitsky1:13:03

        Hmm.

    27. HSHector Serrano1:13:03

        But, like, maybe it put us in a, a bit better of a position, but I mean, there's founders who don't have as brands as big as, as Wispr who have found success with personal brand content. And again, it's like a gateway Uh, into, um, the actual brand. And it's like what easier way to, to make that accessible than through a person who's just telling their story and giving value?

    28. LRLenny Rachitsky1:13:23

        And so interestingly, this is just another, let's say, alpha opportunity to grow, which is the founder-

    29. HSHector Serrano1:13:28

        Yeah

    30. LRLenny Rachitsky1:13:28

        ... sharing their story in a really compelling way.
21. 1:16:01 – 1:20:06

    Why YouTube packaging matters more than production quality

    1. LRLenny Rachitsky1:16:01

       story. Uh, okay, so one last tidbit you shared in this video that we'll share is, so you have this head of content. There's Hector, there's someone filming, videographer, there's a YouTube team, short form. You actually shared the YouTube packaging team. If you had to kind of pick which needs to be stronger, you found the, the YouTube team needs to... Is, is more important than even the quality of the video.

    2. HSHector Serrano1:16:19

       Yeah, YouTube is generally one of the hardest platforms, which is why when you said Instagram or YouTube, I backtracked and I was like, "Actually, YouTube is very important." And that's actually where I started as well, and I saw how much goes into making YouTube videos. Like it's not just, oh, you make a video, you post it, and you put a thumbnail and some sort of picture, and then you're good. It's like at the end of the day, the way I like to think about it is you could have a masterpiece of a video. You can make a Hollywood production movie, but if you put a bad thumbnail and a bad title that doesn't intrigue people to click on it, no one's actually gonna know how good your video is. So you might have invested all this time, all this money, all this energy and effort into making this masterpiece of a video, but if you don't understand how YouTube works and how it's actually gonna rank the highest, um, you're not gonna get the results you want. And that's why I think the YouTube side is so important, because it's not only the thumbnail, it's not only the click-through rate, it's not only the title, the, the watch or the average view duration. It's also like the storytelling, the pacing, how you package it, the intro, how like the thumbnail needs to tie into the video, and there actually needs some, needs to be some sort of payoff. Because if you don't, then you're gonna have more of a drop-off rate, and people aren't gonna stick along to actually watch the video. Um, and like the better your YouTube team is, the easier it makes it for the short-form side. Because typically the people that you're using for short form maybe aren't as... I guess they're not as committed, because they typically have a lot of clients and they're overseas as well. Like a lot of our short-form editors are from Germany. Um, we have one as well in Romania, I think, and then one in Australia. And they're really good short-form editors, but they again wanna get a lot of clicks out, so they're not gonna pay as much of attention to the actual storytelling, and they're not gonna be that good with the clip selection. So if I send them 40 hours of footage, I might not get back the best clips. Whereas if my YouTube team is really good in the post-production, they put a super good 15-minute video, then I can send that to my editors in like a clean slate with no titles, no music, et cetera, and they can just clip the best moments and make it into like really good short-form pieces. Um, and that's, that's kind of the reason why I say the long-form team is the most important part, and it's also the one that has the most likes. Like YouTube videos can ri- can run on for ages and ages. Like even on my own personal channel, I've had a video that's been up now for like five years, and I think like a year ago it was at like, what? 40,000 views. Now it's like 600,000 views. And it's like YouTube videos have so like the longest half-life out of any platform, and it's truly insane. Like some of the videos we post on Tanay's channel might be at like five, six million views in a few years. Um, and that's what's cool about YouTube. It's like a long-term investment.

    3. LRLenny Rachitsky1:18:44

       Uh, I've discovered very similar things with YouTube. It's a wondrous platform. It's maybe the only platform where you can discover, where new people discover you at scale.

    4. HSHector Serrano1:18:54

       Yeah, it's insane. And it's like a lot of these platforms I like... Trust me, I enjoy making content, but sometimes it's like a bit demotivating when it's like, oh, you filmed one piece of content, you posted it, you gotta make the new one. And so obviously with YouTube you have to as well, but you reap those rewards as well long term. It's not like on Instagram, um, where you post a video and in 48 hours it's dead. It's like a YouTube video, you put a lot of effort into it, and we look at some of the charts on Tanay's videos and like we're still getting 10,000 ... views, um, in, like, the last 48 hours, even though it's been, like, three months since it's been posted. And, like, it's still working for us. It's still getting new eyeballs and new customers. Um, so yeah, YouTube is, YouTube is amazing. I, I assume also with how many podcasts you have as well, like, the amount of views you're getting from, like, years and years back or whatever is, is pretty insane.

    5. LRLenny Rachitsky1:19:36

       Yeah. It's fun to watch videos that have kind of climbed the ranks over time. I had, um, Elizabeth Stone on the podcast. She's CPTO at Netflix, and she slowly has climbed the charts to, she's right behind number one now. She's, like, climbing on-- She's approaching number one. And so-

    6. HSHector Serrano1:19:52

       Yeah

    7. LRLenny Rachitsky1:19:52

       ... like, you think these are, like, stuck at that number, but they just keep going, going, and-

    8. HSHector Serrano1:19:55

       Yeah. It's, it's like this, and all of a sudden it just goes like this, and you're like, "Oh, I did not expect that."

    9. LRLenny Rachitsky1:19:58

       I don't know. I don't know. I don't get a lot of those where it just inflects.

    10. HSHector Serrano1:20:01

        No?

    11. LRLenny Rachitsky1:20:02

        But it, it does grow. Or-

    12. HSHector Serrano1:20:03

        Yeah

    13. LRLenny Rachitsky1:20:03

        ... and it's like, wow, I didn't know that was still growing.

22. 1:20:06 – 1:27:44

    Lightning round and final thoughts

    1. HSHector Serrano1:20:06

       Yeah.

    2. LRLenny Rachitsky1:20:06

       Anyway, Hector, this was incredible. Um, before we get to our very exciting lightning round, is there anything else that you wanna share, or anything else you wanna kinda double down on and leave listeners with?

    3. HSHector Serrano1:20:19

       I guess my last point, which I've mentioned a lot, is, like, I would just urge other founders out there to, like, give a chance to, like, young talent. And yeah, just, just find those people, believe in them, trust in them, give them opportunities, and yeah. Like, not only will they turn into some of your best A players, but also the amount of loyalty, um, they will have to you is quite incredible. And whether they stay at your company or they go, go on to do other things, like, they will always be there to help you or help you bring in other young talent, um, or guide you in the right direction when things-- when a new alpha is out there. Um, and yeah, I'm super grateful to Tanay and Daniel and the whole Wispr team for, like, taking a shot on me, and there's no better place I think I, I could've, I could've landed, and I'm, like, forever in debt or however you would say that, but I'm just super grateful, um, for the, for the opportunity I was given.

    4. LRLenny Rachitsky1:21:08

       That's beautiful. Well, with that, we've reached our very exciting lightning round. I've got five questions for you. Are you ready?

    5. HSHector Serrano1:21:15

       I've seen these. I've seen these in the, in the, in the podcast. [chuckles]

    6. LRLenny Rachitsky1:21:18

       Won't be a surprise. Uh, okay. Well, here we go. First question, what are two or three books that you find yourself recommending most to other people?

    7. HSHector Serrano1:21:26

       One of my-- I'm gonna give one book. I'm gonna give one really good book, which might be a, a, a cliché one, but Naval Ravikant's Almanack. I remember reading that about two years ago, or maybe a year and a half ago. Um, and it was, like, kind of in this moment where I wasn't-- Like, I was sure I wanted to do content, but I also didn't understand why it was important or why it mattered so much. And, like, I read it the first time, didn't really make that much sense to me. And then I, like, gave it some time, and then things started to, like, line up, like it said it kind of in the book, and, like, how, um, how, how does he say it? Like, media is, like, one of the best forms of leverage because you don't have to ask for permission. It's permission-less leverage, and you can just make stuff and put it out in the internet, and it will continue to work for you. Um, and, like, I started to see that compounding effect over time of, like, me putting myself out there, and it's a book I continue to find myself coming back to and reading. Um, I bought it for my little brother as well recently. Um, and it's, like, something I'm, I'm always sharing with friends and always passing on to them to read as well. And I feel like it, it gives direction a lot to, like, young people as well, um, in this crazy world that we live in. So, I'd definitely say that's one of my favorite books I've, I've read.

    8. LRLenny Rachitsky1:22:36

       Yeah. Naval went through this era of just sharing this profound advice on Twitter, and then he kinda slowed down and, and I love that there's a book that collects it all. Um, and I love that so much of advice you don't like. You see it and you're like, "Yeah, it's fine," and then you think back to it. Wow, he was so damn right.

    9. HSHector Serrano1:22:50

       Have you, have you read, uh, what's it? Ego is the Enemy?

    10. LRLenny Rachitsky1:22:53

        Is that a, is that a book, or is that one of his lines?

    11. HSHector Serrano1:22:55

        No, it's a, it's a new book. I think, I think it's called something like... I was just wondering if you read it because I was interested-

    12. LRLenny Rachitsky1:22:59

        No

    13. HSHector Serrano1:22:59

        ... in, in, in reading it. I was about to buy it, um, I need to go to a bookstore. There's not that many bookstores in Puerto Rico. Um, but yeah, I'm looking for a new book, so if anyone wants to drop some comments on the video, um-

    14. LRLenny Rachitsky1:23:08

        Okay

    15. HSHector Serrano1:23:08

        ... let me know.

    16. LRLenny Rachitsky1:23:09

        Does Amazon deliver to Puerto Rico?

    17. HSHector Serrano1:23:11

        Yes, but-

    18. LRLenny Rachitsky1:23:12

        Okay

    19. HSHector Serrano1:23:12

        ... it's, like, a bit, it takes, it takes a while. Living on an island.

    20. LRLenny Rachitsky1:23:16

        Yeah.

    21. HSHector Serrano1:23:16

        Everything is a, a lot lower, a lot slower.

    22. LRLenny Rachitsky1:23:18

        Frozen times.

    23. HSHector Serrano1:23:18

        Less dopamine rush. You don't get-

    24. LRLenny Rachitsky1:23:20

        It's better for us

    25. HSHector Serrano1:23:20

        ... 24-hour delivery. [chuckles]

    26. LRLenny Rachitsky1:23:22

        I love that. Okay, next question. Do you have a favorite recent movie or TV show you have really enjoyed?

    27. HSHector Serrano1:23:26

        I just watched the Elizabeth Holmes movie with-

    28. LRLenny Rachitsky1:23:29

        Me too

    29. HSHector Serrano1:23:29

        ... uh, my girlfriend.

    30. LRLenny Rachitsky1:23:30

        No spoilers. That's not-

Episode duration: 1:27:46