How Wispr Flow Built a Paid-UGC Engine: Hector Serrano's Playbook for SaaS Growth
Lenny's Podcast
Hector Serrano joined Wispr Flow at 19, before the product had found product-market fit, and now runs its paid user-generated content (UGC) program and the founder's organic channels as head of content. In this conversation with Lenny Rachitsky, the central question is what is actually working in growing a B2B SaaS product right now. Rachitsky cites reported figures that Wispr Flow's revenue grew 30x in the past year and that the company recently raised at around a $2 billion valuation. Serrano's answers cover three areas. The first is a performance-based paid-UGC model borrowed from e-commerce. The second is a view of hiring that favors young, unconventional marketers over polished résumés. The third is a strong preference for human-made creative over AI output.
Serrano starts by crediting the rest of the team and describing his own role as a small part of the business. He handles content. On the paid side that means creative, not media buying. He also manages the organic channels of founder Tanay Kothari, such as YouTube and Instagram.
Product first, then fuel
Asked what has driven growth, Serrano says the most important factor, "maybe a bit corny," is the product itself. Wispr Flow has been product-led from the start. Serrano recalls the company having a few thousand users early on. About six months in, it started catching on, and Kothari remarked that they had found product-market fit. Every channel added after that, organic or paid, was "more fuel to the fire."
Founders sometimes visit the office or reach out asking for "the hack." Serrano's answer is that there isn't one. If a product isn't growing organically and has to be forced, the team may need to go back to the drawing board. They should ask whether it is really valuable and how it is positioned. Rachitsky suggests that finding creators who are genuinely excited about a product is almost a test of product-market fit in itself. Serrano agrees and adds that low creator churn is part of the signal. Talking about something you don't believe in gets boring quickly.
Why turn on paid ads early
Serrano argues that paid is one of the best channels to invest in early. He credits this lesson to Matt Swulinski, Wispr Flow's former head of growth, who is now at Viktor. Matt brought an e-commerce approach to SaaS. Many SaaS companies are afraid to turn on the paid engine. Serrano says that doing so teaches you quickly whether your messaging resonates and whether you can convert cold traffic into users.
His reasoning is that most companies aren't skilled at organic content. Unless you have young people on the team who understand packaging and production for these channels, organic gives you few clear numbers on whether the product has legs. Paid, tested within your budget, gives a clear signal. If you can turn cold traffic into paying users, Serrano says, the same messaging should also work organically with more optimization.
Some teams fear that spending heavily will saturate their market or ideal customer profile (ICP). Serrano's response is that saturation mostly comes from a lack of creativity. There are always new messaging angles and new ICPs to target if you are "savvy enough with the angles."
The organic UGC experiment that came first
Serrano traces the current program back to an earlier experiment. In early 2025, Wispr Flow had a marketing intern named Tobin Tang. Tobin had studied finance, wanted to be a lawyer, and had only basic UGC experience. Kothari gave him a budget and told him to throw things at the wall. Several projects failed. Then Tobin found success with organic UGC.
Serrano explains the model this way. A brand recruits a group of creators who make videos about the product. The creators post those videos on their own alternate TikTok or Instagram accounts, for example an account named something like "Lenny Whispers." They get paid on a CPM basis, perhaps around $2 per thousand views, with the rate tapering at higher view counts. According to Serrano, Tobin's program reached roughly 500 million views in about two and a half months at very low CPMs.
It "worked decently well," but Serrano says this was a period when everyone chased vanity metrics. The views didn't translate into many conversions. The product was also hard to sell to the students who made up much of that audience. Finding someone to replace Tobin after he left would also have been hard. So Wispr Flow killed the program. Serrano stresses that he isn't against organic UGC. He says Tobin later "cracked the code" at Polymarket by going beyond purely top-of-funnel concepts. It just wasn't delivering what Wispr Flow wanted.
Applying the playbook to paid, via Trybe
About seven months before the interview, Serrano noticed that paid was working well. He was still making all the paid assets himself. He wondered what would happen if they took Tobin's playbook, a community and roster of creators paid on performance, and applied it to paid ads. The ads would pitch the product more directly than text-on-screen organic content did.
Around then he came across Trybe. Serrano says it was started by Lukas Pakter, who had earlier grown the clothing brand SquidHaus quickly through TikTok Shop. TikTok Shop lets brands pay creators on performance, but nothing equivalent existed for Meta ads. Pakter built an internal tool to run creators' ads on Meta and pay them based on results, then opened it to everyone. Wispr Flow was one of the first companies on it. Serrano called it a no-brainer: "the TikTok Shop method, but for Meta ads." Because SaaS companies can't use TikTok Shop, he sees it as opening a new performance-based channel for them. Wispr Flow now launches 500 to 600 ads a month from the program.
The mechanics differ from organic UGC in one key way. Creators make a video about Wispr Flow, and Wispr Flow runs it as an ad on Meta and other platforms. The creator is paid a share of how that ad performs, not by views on their own account.
Paying creators: percent of spend, percent of GMV, and the smart retainer
Serrano distinguishes two payment bases. For a SaaS product, especially a freemium one where attribution is murky or can take a week or two, Wispr Flow pays creators a percentage of ad spend on their ads. That protects creators from a situation where their ads drive conversions that never get attributed to them. For e-commerce products like a water bottle or a T-shirt, where it is easy to tell whether a purchase came from a specific ad, a percentage of GMV makes more sense.
Pure commission is demoralizing early on. A new creator might make 30 videos and earn only $100. Serrano also observes that the best creators are often the ones who stuck around longest and learned how the model works. So Wispr Flow adds what it calls a "smart retainer." In his example, a creator commits to 25 videos with a $1,500 floor. If the creator hits the quota but earns only $500 in commission, Wispr Flow tops them up by $1,000. If they earn $3,000 in commission, they keep the commission and get no retainer. This keeps new creators committed through their first few months. Serrano says creators often "break out" after three or four months and earn purely on commission. From the brand's side, that is ideal because payment then flows only to the best-performing videos.
Earnings are uncapped. Serrano says some creators now make about $13,000 a month, more than many full-time influencers, even though they may have only 1,000 to 2,000 followers. Wispr Flow pays out every seven days. Serrano calls this a hack for motivation: the faster creators get money and the "dopamine rush," the better.
No briefs: creative freedom and compounding knowledge
As a creator himself, Serrano believes the standard approach to UGC kills its value. He admits Wispr Flow sometimes did this too. Brands send creators long briefs telling them which hooks to use, what not to say, and how to film the product. A 10-page guideline removes the creative part of the job, and he says nothing is more demotivating. A creator who is trusted and given room to make content "how I see best fit" will produce better work.
Working with the same creators month after month also compounds. Serrano says some of his creators understand the product almost better than he does and come up with ideas he never would have. When Wispr Flow launches something new, like its note-taker, he can drop it in the Discord and ask for videos. He doesn't have to recruit and brief a fresh set of creators who will be gone the next month.
Rachitsky asks whether the person leading this work should have made ads themselves first. Serrano says yes. He personally made every Wispr Flow ad for about a year and a half, "hundreds and hundreds" of them. He compares non-content people briefing creators to a non-engineer telling engineers how to solve a problem.
Step by step: building the group from zero
Serrano walks through the full process.
Set up the structure. Choose percent of spend (SaaS) or percent of GMV (e-commerce), and set up the group on a platform. He prefers Trybe.
Recruit off-platform at first. A new brand on Trybe has no payout history and no creators. Serrano notes that Wispr Flow's Trybe profile shows roughly $300,000 paid out across only 50 creators, which drives a lot of inbound. A brand showing $0 and zero creators will struggle to attract good people. So he went to Instagram and searched keywords tied to his niche, such as "UGC creators," tech, 9-to-5, lawyer, doctor, or whatever fits. He went down rabbit holes and checked the following and follower lists of creators he liked, because good creators tend to know other good creators. Over about a week he sent 150 to 250 targeted, manual DMs. He warns against mass-messaging software. Moving fast with automation, he says, brings back "slop" and bad creators. From those DMs he expects five or six really good creators. He says he hasn't needed to do outreach since.
Pick creators to fill specific gaps. Serrano adds that the goal isn't just "start with five." It is to look at your ad library and product and ask which audiences and messages are missing. A hundred similar creators won't scale because everything will look the same. Five creators who each speak to a different audience produce net-new concepts. Wispr Flow's roster now includes moms, lawyers, engineers, sales reps, agency owners, and one creator Serrano describes as an eight-figure e-commerce founder in his mid-40s with kids, who makes ads simply because he loves the product.
Build culture. Activities include weekly meetings, creator coaches who keep people engaged, giveaways, and a planned retreat in San Francisco where Wispr Flow is flying in top creators from around the world.
Grow slowly. Wispr Flow went from five to 10, then 15, then 20 creators, adding five or six every few weeks. As payouts accumulated, applications started coming in through Trybe. Serrano says he now gets about 1,000 to 1,500 applications a week and accepts only one to three. The group is capped at 50. Creators also get $100 for each referred creator Serrano accepts. When his LinkedIn post went viral, people called the referral program an MLM-style scam. He rejects that comparison. Nobody is paid simply for bringing in bodies, the group is capped, and the bonus is a thank-you for helping the program grow.
Coach against copying. Creators can see which ads are getting the most spend. That transparency backfires if they start cloning the top performers. Serrano explains that Meta's Andromeda system groups highly similar ads together. He says it scans an ad repeatedly, pulling the transcript, individual frames, and on-screen text. Similar shirts, settings, or words lead to fast fatigue. So he keeps reminding creators that the top earners got there by experimenting and leaning into their own interests. Copying them just ranks your ads beneath theirs.
His favorite example of what freedom produces came from a creator who put a keyboard outside a window on a roof in the rain. The text read "What is my keyboard trying to say?" The camera panned to a laptop where the "raindrops" typed random words, ending with "Download Wispr Flow." It became one of their best-performing ads. "I don't even know how we came up with that," Serrano says. He claims no two ads in their library look the same.
Outreach and onboarding as relationship-building
Serrano's best source of early creators was people already following the brand or already sitting in its DM requests. They likely like the product, so a simple message works: he saw their content, enjoyed it, and would love to have them in the creator group. He deliberately doesn't lead with the performance-based pitch. Creators are still skeptical of the new model, and even more were six or seven months ago. If they respond, he sends a simple PDF explaining the structure, pay, and what top creators earn, then gets on a call. He sends DMs from either the brand account or his own. He notes that hiring someone with an audience doubles as a recruiting channel. He has filled many roles by posting on his Instagram stories.
The onboarding call is built to counter what he sees as creators' usual experience: purely transactional work where they make a video, get paid, and never hear from anyone again. Most creators work remotely and crave community. He first asks how they got into content and why they enjoy it. Then he walks through a slideshow. He introduces himself and his creator background so they respect him. He introduces media buyer Eric Zaworski, explains the product, and explains how Trybe works from submission to approval to running as an ad. He mentions the seven-day payouts and shows example ads. He gets them onboarded during the call itself, comparing this to closing a sales deal. You don't want to get someone excited and then have to chase them.
Serrano believes the companies that win long-term will be the ones with the best creator relationships. Brands that pay late, don't pay, or block creators get a reputation quickly and lose access to the best people and terms. He says Wispr Flow tries to treat agencies and other external partners with the same respect.
Team structure
To start a program like this, Serrano says you mainly need two people. One is a creative lead like him, who handles communication with creators, generates concepts, and approves videos. The other is a media buyer who structures the ad account and optimizes spend across Meta, LinkedIn, YouTube and elsewhere. He calls it rare to find someone who does both. He describes himself as "not a numbers guy" and is glad he doesn't have to stare at Ads Manager.
Early on, the marketing team was CMO Daniel McCallum, Matt as head of growth, and Serrano as the sole creator, plus some external agencies. Over time they added design, an in-house director for films and launch videos, PR, a creative partnerships lead for influencers, and a celebrity talent manager. Serrano says the company has passed about 120 full-time employees, up from roughly four when he joined. Marketing is around 15 people. The team is flat with no middle management. Serrano jokes that he feels sorry for Daniel's calendar given all the direct reports.
Why volume matters, and why UGC is only one leg
Serrano frames the UGC group as an extension of himself. He was effectively an in-house UGC creator, burning out after more than a year as a "one-man show" while ad spend kept rising. Higher budgets also burn through creative faster. He says that in 2024 an ad could run for 12 months. Now, with Andromeda and Wispr Flow's spend levels, an ad is typically "dead" after about $100,000 in spend, which can happen in two to four weeks. By his estimate, the account has around 5,000 lifetime ads and 800 to 900 live at once. UGC is only part of the mix. The library also includes statics, celebrity and influencer videos, in-house ads, launch videos repackaged as ads, and founder-led content.
He also says ads are "almost weirder than organic." He can roughly predict organic performance, but ads he thinks are strange sometimes become top performers. That is why he keeps the acceptance bar low and tests widely. Some of the best ads he made a year ago are long, ugly vertical screen recordings of someone using the product with text on top.
Does it work for technical and enterprise products?
Serrano believes the model works for any company if you find users who can speak to the users you want to acquire. A common mistake is treating UGC as "college kids making content." For a dev tool, the user is probably an older technical person, and an 18-year-old won't be convincing. For technical audiences, he says, "the more boring and the uglier the ads are, the better they will perform." A plain screen recording, even 30 seconds to a minute long, can work. The same applies to an expensive sleep product. People won't buy a $3,000 item from a teenager. They want someone with the same work and problems. He concedes it gets harder the more upstream, expensive, or niche the product is.
On enterprise, he argues that companies are made up of individuals. Content can reach one person who downloads the app and tells a coworker. Usage spreads inside the company, and eventually there is an enterprise deal to pursue. Rachitsky reads this as best suited to bottom-up, product-led products like Wispr Flow or Notion rather than Workday or Salesforce. Serrano doesn't push back.
Serrano also argues that creators with no following can be better investments than influencers. Big names are often seen as sellouts "getting a bag." An unknown person speaking naturally through a partnership ad feels more genuine.
Hiring the modern marketer: résumés lie
Rachitsky mentions a tweet calling a person like Serrano the hardest role to hire for right now. Serrano compares himself with Tobin. Serrano had a 2.5 GPA, didn't attend a top school, and played Division 1 sports. Tobin had a 4.0 and went to Waterloo. Both turned out to be strong marketers, which their résumés wouldn't have predicted. His advice to anyone looking for "someone like me" is not to try, because there is no defined path. Find a kid with "some crazy background, and the crazier the better," who also has proof of work.
His criteria are simple. Is the person hardworking? Are they a good human who fits the culture? Have they grown an account to roughly 10,000 to 15,000 followers? He says a following shows they understand consistency, trends, filming, and editing. He treats Instagram as a stronger signal than TikTok, which he calls easier to grow with "brain rot" content. He also rates YouTube highly and later says he underrated it at first. As evidence that platform skills transfer, he notes he barely posted on X until two weeks before the interview. He went from about 500 to roughly 18,000 followers by treating it as a volume game: short posts, a personal style, and real value. He thinks moving from text to video is harder than the reverse. He pushed Eric to start filming, and Eric struggled for the first month.
He also stresses patience. Serrano says he was "all over the place" for his first seven months, and there were hard conversations with Daniel. The team still gave him room to fail as long as he kept learning, just as it gave Tobin money and time until something stuck after about two months.
On mistakes companies make, Serrano warns against job listings with $200,000 to $250,000 base salaries and long requirements. He says those attract the wrong people. He and Tobin were interns earning nowhere near that, hungry to learn. He recalls that on his second call with Kothari, as a 19-year-old who had never worked at a startup, he asked for equity. He says Kothari laughed and said, "I like you, man." Serrano reads that as the naive, hungry signal companies should look for. Rachitsky quotes two of Serrano's tweets. One says that companies looking for the marketer with the best résumé will end up hiring a bot. The other says the most successful people Serrano has met are "delusionally confident," outwork everyone, and love what they do.
The case for young talent and a sports-style pipeline
Serrano points to Jimmy Farley, whom he calls one of the TikTok Shop "OG" figures. Farley built an agency from around age 17, which Serrano says was acquired by Physician's Choice. Older e-commerce founders around Farley talk about the "alpha" of having someone like him nearby. A 30- or 40-year-old founder can't understand what an 18-year-old in Discord chats and scrolling Instagram all day knows about what's working. Even if founders dive into TikTok Shop or Trybe themselves, Serrano thinks they'll struggle to connect with creators and would do better delegating. He adds that Kothari still regularly asks him what's working on Instagram. Serrano takes from this that you never get too smart to keep learning, even from a 19-year-old.
His own path illustrates the point. He quit Division 1 soccer and, three days later, having just turned 19, applied to about 200 creator jobs on LinkedIn and landed at Wispr Flow. In one of his first weeks, during launch prep, Kothari messaged him in calculus class. Serrano slipped out to the bathroom to join a Slack huddle. The launch video wasn't working, and Kothari wanted it re-edited with "Gen Z vibes" in CapCut or similar tools. Serrano spent his first year picking up random tasks with no clear role and says it took about a year to feel comfortable. His immigrant parents wanted a traditional finance career. The next summer he took a finance internship in New York while also juggling two summer classes and Wispr Flow. He hated the internship within two weeks and started sneaking out to cafés in SoHo to work on Wispr Flow and his own content. Things began to "click" from there.
He draws on his soccer background, including time in a La Liga academy in Spain, MLS Next, and Division 1, to argue that startups should recruit like sports clubs. Clubs scout young talent, develop them over years, and promote them. He says many companies have dropped internship programs, which he considers among the most valuable and least expensive things a company can do. He cites Lamine Yamal's success as a teenager as evidence that betting on young talent pays off. He closes the interview urging founders to give young people a chance. In his view they can become A players, and they bring unusual loyalty whether they stay or move on.
"The best marketers are allergic to AI"
Rachitsky notes that AI barely came up and asks about Serrano's tweet saying the best marketers are allergic to AI. Serrano's argument is that even top AI labs use large teams of humans to produce their final assets, such as videos, Figma designs, editing, and post-production, though much of their research and internal work may be automated. For an AI company like Wispr Flow, whose pitch is helping people work better and sound more like themselves rather than replacing them, AI-generated "slop" ads, AI influencers, and AI statics would land badly given how many people are wary of AI. He cites cases where companies' AI-made animations or assets backfired because of typos or jumbled writing. He says the risk isn't worth the reward.
He clarifies the scope: the concern is the final creative output people see, which he doesn't think AI should touch "yet." Even Matt, whom he calls the most AI-bullish person he knows and someone with "the most automations I've ever seen," keeps a human on the most important final 10%. With so much automated volume everywhere, Serrano argues that focusing on quality over quantity makes it "so easy to cut through the noise."
Founder-led content and the long game
His example is Kothari's YouTube channel. Serrano says it launched about three months earlier, and five videos in it had millions of views and about 20,000 to 21,000 subscribers. Many teams assume they must post three times a week. He says the opposite worked: fewer videos, each telling a good story, with purpose, strong packaging, and humans touching every part.
His argument for founder-led content is that "people buy from people." He uses George Heaton, founder of the clothing brand Represent, as a personal example. Because Serrano knows Heaton's routine, values, and work ethic, he would buy from Represent over a brand he only sees in an ad. Founder content creates superfans among existing users and slowly brings in new people who buy into the mission before trying the product. He calls it a long-horizon investment. You can't start selling right away or people switch off. Instead, you over-share, over-deliver, and perhaps make a soft sell a year in, such as a discount code to thank viewers for reaching 100,000 subscribers.
On storytelling, Serrano says every company has a mission. Wispr Flow's is reaching one billion daily active users. All content should tie back to it, like episodes of a Netflix series with one overarching theme. He describes it as a public version of the product roadmap, showing the ups, downs, and struggles. Episodes have ranged from the note-taker launch, to Kothari wedding shopping in India while working remotely, to a "week in the life" video and a whiteboard breakdown with Serrano. Rachitsky suggests this is easier for a company people already care about. Serrano concedes that may have helped but believes founders with smaller brands can succeed too.
He also argues organic and paid reinforce each other. Citing the common idea that people need around seven touchpoints before buying, he says someone who has watched long-form YouTube, seen the founder's reels, and read LinkedIn posts is more likely to convert on the first ad they see. Rachitsky notes that paid then gets credit for the conversion, and Serrano agrees.
The founder-content team, and why YouTube packaging matters most
Rachitsky summarizes the team from one of Serrano's videos. There is a head of content (Serrano), a videographer, a YouTube team that packages long-form videos, and short-form editors who cut clips. Serrano hired almost everyone through his Instagram stories. That includes the 24-year-old videographer, Alex. After a story post drew around 80 replies, Wispr Flow flew Alex out to San Francisco from Australia, where he was vacationing, on three days' notice. The YouTube agency also came through Instagram.
Asked which role matters most, Serrano picks the YouTube packaging team, over even the production quality of the footage. You could make a "Hollywood production," he says, but a bad thumbnail and title mean nobody clicks. Packaging covers click-through rate and title, but also average view duration, storytelling, pacing, the intro, and making sure the video pays off the thumbnail so viewers don't drop off. A strong long-form team also makes short-form better. Wispr Flow's short-form editors, based in Germany, Romania and Australia, often juggle many clients and optimize for output rather than story. If Serrano sends them 40 hours of raw footage, he may not get the best clips back. If he sends them a well-cut long-form video without titles or music, they can pull the strongest moments.
He also sees YouTube as having the longest half-life of any platform. One video on his personal channel has been up about five years. He says it was around 40,000 views a year ago and is now around 600,000. Some of Kothari's three-month-old videos still pull about 10,000 views every 48 hours. Instagram posts, by contrast, are typically dead within two days. He predicts some of Kothari's videos could reach five or six million views in a few years. Rachitsky shares a similar experience. His episode with Netflix CPTO Elizabeth Stone has slowly climbed to nearly the top of his channel.
Lightning round
Serrano recommends The Almanack of Naval Ravikant. It didn't click the first time he read it, but the idea of media as "permissionless leverage" later matched what he saw as his own content compounded. He has bought it for his younger brother. He also says he is curious about Ego Is the Enemy but hasn't read it yet. He recently watched the Elizabeth Holmes movie with his girlfriend and enjoyed it. His favorite AI product is Miso, a travel agent, with no affiliation. He says he has taken around 55 to 60 flights and about 89,000 miles this year. When he once slept through his alarm and missed a flight from Puerto Rico to San Francisco, he texted Miso and was rebooked within about two hours at no extra cost. He notes that Miso has humans on the back end with airline connections for escalation.
His life motto comes from Steve Jobs: you can't connect the dots looking forward, only looking backward. Serrano says he was never the smartest kid in school, had severe ADHD, and felt lost for months after losing soccer, even while at Wispr Flow. He didn't understand at the time why he had picked up a camera at 16 or started posting on YouTube. Looking back, he says, it all makes sense. His closing advice is to keep going, and he invites listeners to follow along on X, Instagram, and YouTube.
You have been doing this insanely incredible job growing Wispr Flow over the past couple years.
Wispr Flow at 19.
I looked up creator jobs on LinkedIn. I saw 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, "I want equity in Wispr." And Tanay laughed and was like, "I like you, man."
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.
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.
You actually had this tweet the other day: "The best marketers are allergic to AI."
If we go out and start making AI slop ads, it's probably not going to 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.
Let's talk about paid UGC. You were getting influencers, creators to create a pitch basically for Wispr.
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 $13,000 a month.
The hardest role to hire for right now is someone like you.
I think if you just think that looking for someone with the best grades or the best school is going to get you the best hire, you are in for a rude awakening.
Hector, thank you so much for being here. And welcome to the podcast.
Thank you. Thank you. I'm excited to be on.
I'm even more excited to have you here. What I want to 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. I saw this stat that revenue at Wispr Flow grew 30x in the past year, which is absurd. You guys recently raised at something like $2 billion in a very competitive market. Clearly you figured something out. You've started to share some of the strategies that you've been deploying on X. And so we're going to be going deeper into the stuff that you've seen work.
First of all, give us a sense of what it is you're responsible for at Wispr Flow. It's kind of your job there, and what do you work on?
First of all, I just want to give a lot of credit to the other members of the team. What I touch at the end of the day is a very small part of the business. And that's mainly content as a whole. 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 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, like YouTube and Instagram.
Okay, awesome. Something that I've noticed about you and something that I think is really rare these days is 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 figured out how to do that yourself. Also with 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've figured out.
So just zooming out first, talk about the growth levers that you have been spending time on. What has been working recently in growing Wispr Flow slash can work for other B2B SaaS products?
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. 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 six months in, I remember Tanay said, "Wow, we really found PMF." We struck gold. 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 through trial and error, doing a bunch of different things, me testing a bunch of channels, other people testing a bunch of channels, 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, influencers, in-house videos, founder storytelling. But yeah, paid ads as a whole, whether it be through Meta, LinkedIn, YouTube, etc., 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.
Awesome. Okay, so let's dive in there. But first, and I think to your point, it's really important to say none of this will really work if your product isn't exactly great, if there's not real organic product-market fit already. I imagine this can work for a little bit, and then it just fades away if the product isn't great. So, I guess, is that just lesson one? This needs to be working on its own before you start investing in paid?
Yeah, exactly. I have a lot of founders sometimes reach out or come by the office, or friends, and they're like, "What's the hack? How did Wispr grow so fast?" And it's like, no disrespect to other products, but if you're not having that growth early on and you're having to force it a little bit too much, then maybe you have to go back to the drawing board a little bit and rethink how you're actually positioning the product. Is it actually valuable to your users? Why isn't it growing by itself organically? And yeah, there's really no hack besides having a good product and then adding more levers to pull from.
So, let me ask, when do you think it makes sense to start investing in these inorganic channels?
Well, I think paid is actually one of the best channels to invest in early on. And I learned this from Matt, who's actually our ex-head of growth at Wispr. He's now at Viktor. And a lot of his lessons and lessons that I've learned from him is taking this e-com approach to SaaS, which a lot of companies are scared to turn on the paid engine. And what happens when you actually turn on the paid engine is you actually learn a lot faster if the messaging actually resonates with your audience. Are you actually able to convert this cold traffic into users?
And at the end of the day, most companies aren't that skilled in organic content because it is something very new. And unless you have really young people on your team who really understand these organic channels really well, 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, etc.? So, I think paid makes sense from the get-go, obviously testing within your limits and your budgets that you have. But yeah, if you're able to see, "I'm able to turn this cold traffic into paying users," then you have a clear signal there that this same messaging or this product will also work on organic if you optimize things a bit more.
I want to come back to that, just 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 paid has been around for a long time, running ads on Instagram, Facebook, TikTok, all these things. 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.
Yeah, 100%. And a lot of times people also get scared because they'll say, "Oh, I don't want to turn on the paid engine yet or spend a bunch of money because then we're going to reach a point where we oversaturate this market or this ICP." But at the end of the day it's just getting smarter with how you're, again, positioning the product. And there's always new ways or new messaging, new ICPs you can target. And you won't really reach saturation if you're savvy enough with the angles that you're approaching your content with, or how you're approaching that paid mechanism, I guess.
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Okay. So, let's actually dive into this. Let's talk about paid UGC and paid in general. What's the overall strategy that you have employed that has worked so well?
I think it would be good to start maybe from what we learned previously, actually. So, where do we go back to? I think this was early 2025. We had an intern named Tobin. He's a good friend now. I don't know if you've heard of him. He also went pretty viral a while back. He ended up joining Polymarket. But basically, Tobin came on as an early intern marketing hire. Didn't really have any experience besides some basic UGC. I think he was studying finance and wanted to be a lawyer. And he came in, and Tanay just gave him 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 the Clue era when there wasn't that many people doing it successfully.
Explain organic UGC. What is that exactly?
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 Whispers. And then you just upload your videos into there, and then you get paid based off of a CPM metric. So, maybe it's, I don't know, $2 per thousand views. And then it tapers off as you get higher and higher. And yeah, Tobin set that up for us. And I think in two and a half months it was 500 million views.
Super low CPMs, and 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 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. He cracked the code with organic UGC and not just doing very top-of-funnel 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 going to be really hard to find someone to take Tobin's role after he left. So, we're like, "Let's just kill this." And then again, paid was working relatively well for us. So, that brings us to where we're at now. Not now, but 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 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?" I mean, not even just middle of funnel, because you need everything in paid ads, but more just pitching the product straight on instead of just screen-on-text ads.
And then I stumbled upon Trybe, which, I don't know if you want me—do you want me to get into that now?
Yeah, talk about Trybe. And it's T-R-Y-B-E, right?
Yes, T-R-Y-B-E. So, Lukas Pakter, he's this guy who started Trybe, but before that he actually started SquidHaus, 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 new channel for SaaS companies to be able to run performance-based ads.
And yeah, we hopped on there, built out our program, and if you fast-forward to now, we're now launching 500 to 600 ads every single month. And it's been a great process. Obviously, that's skipping a lot to where we're at now, but just wanted to 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.
Okay, amazing. We're going to 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.
No, so they post it on their channels.
They post it on their channels.
Yeah, yeah. So, it's CPM-based. So, let's say, again, we bring you into the group, and then you make your own channels on TikTok and Instagram, and it'll be like Lenny Whispers or Lenny Talks. It can be anything really, but you won't then post it on your main Instagram. You'd post it on an alternate. And then we would pay you CPM-based.
Okay, so the big difference here is instead of CPM-based, which is basically views-based, they take a percentage of spend, or...
Yeah, a percentage of spend or GMV, depending on if you're in SaaS or if you're e-com, something like that.
Awesome. Okay, cool.
Yeah.
So, you've shifted to this model. It's basically performance-based UGC. So, just to be very clear about how this works, you find—I think you have something maybe like 50 creators right now.
Yeah, right now we have 50.
Okay, and we'll talk about the progression that you recommend, starting with a couple. So, you find creators, 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, and then they get a cut of how that ad performs.
Exactly.
And then you have two approaches to the cut they take. Talk about that.
Yeah, so obviously, we don't want to just pay creators just off percentage-based, 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 stuck around for the longest and they've understood how the model works.
So, one thing we actually have included is called a smart retainer. And what this is is basically us saying, "Okay, we're going to back you as a creator. And let's say we're going to do 25 videos and we're going to pay you $1,500. As long as you hit that quota of videos, we'll pay you that money."
But 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, just 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 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 commission-based, which for me as the guy running the program, or if you're a brand owner, that's the best thing because you're paying them pure profit 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. 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 film the product." And when you send the 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. And there's nothing more demotivating than that.
And I know as a creator, 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 going to 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 want to work in our group. And we also keep it really tight-knit. So, it's 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 for a video. We're not paying them $50 a video. It's not $1,000 for the month. 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 full-time influencers. And they might have like 1,000, 2,000 followers on their own Instagram accounts. But this has just been a way for any creator who's talented to be able to make real money.
Awesome. And the way you do it is if it's a shopping sort of product, you give them a percentage of GMV. And then if it's the B2B SaaS product, you give them a percentage of ad spend.
Especially if you have a freemium product where it's hard to track direct conversion because we also don't want to 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 paid what they're worth. And with a product like Wispr where it's kind of hard to track those attributions or it might take a week or two, it's best if we just keep it at a percent of ad spend. But obviously if you're selling, I don't know, a water bottle or a T-shirt and it's really easy to track whether a person came from this ad or that ad and if they purchase or not, then it makes more sense to do a percent of GMV.
So, the innovation here that has worked really well is giving the creator a piece of the action of the success of their ad.
Exactly.
Awesome. And then also capping the downside so that they can actually spend time doing this versus being worried that they're not going to make a living.
Yeah, exactly. Because a lot of the times these creators end up having to constantly be negotiating with brands or working with new companies, learning new things. And not only are these creators all power users, but they get to work with the same company every single month. So, just think about the compounding effect of how much better the videos get over time instead of, "Oh, you're this brand who's maybe launching a new feature." And you're like, "Okay, let's scramble to find new creators."
And if you already had that internal group of creators who already know your product and already believe in you, and some of my creators understand the product better than me almost, and they come up with ideas I never could have come up with. So, if you just have that internal group already, it's so easy that when we launch a new thing, whether it was the Wispr note taker or all these different features 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. So, yeah, it just makes for a great experience both on the brand side and the creator side.
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.
Yeah, and it's just easy to burn out as well as a creator. If you're talking about something you don't believe in, it can get boring really quick.
Yeah, it's almost a test of product-market fit. Can you find creators that are excited about—
Yeah, and low churn.
Yeah.
That was honestly, because 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, which I guess that's a testament to how much I loved Wispr. I didn't go crazy. And yeah.
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 creators to create the ads?
Yes. I thought it was important because it goes back kind of to a point I mentioned earlier where a lot of people who've never worked in content or who have never worked with the creators end up being the ones briefing them and telling them what to do. And you would never have someone who's not an engineer telling the engineering—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." And they're going to be like, "What is this guy telling me?"
Okay, so let's go down this tangent of, to find someone like Hector, what does a profile look like if you were to find a Hector to lead this work at your company?
Because it's 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. If you look at both of our resumes lined up next to each other and I asked you to pick one or the other, 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. 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 1 sports, Tobin didn't. And 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 looked at the face value of our resumes.
But I think Wispr has done a really good job of seeing one or two really key things. And also being able to see, okay, is this person a good fit for the culture? Do they seem hardworking? If they have the same values or the same culture as people already at Wispr. 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 embody those character traits perfectly.
And you might be asking, okay, well, what are the traits I need to look for in a good marketing hire? And honestly, it's not that complex. 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? That's how basic it is. 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 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, etc.
And yeah, I think that it comes down to style. Do they seem like a hard worker? Are they a good person? And do they have those minimum 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, you're not where I want you to be, you're gone. 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 all over the place. I still joke about it with Daniel how there was some hard conversations here and there where you're like, "What's Hector doing?"
But yeah, they gave me the freedom to keep experimenting and keep trying new things. And it didn't really matter if you failed as long as you're consistently learning and getting better and getting better. And 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.
Okay, this is extremely valuable. There's this tweet the other day that came out of just 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, 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.
I would say Instagram is probably the highest signal because TikTok is typically a bit more brain rot content. And Instagram's 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's probably a higher signal than TikTok. It's pretty easy to grow on TikTok posting some brain rot stuff, I would say.
I see. What about X and YouTube?
YouTube is decent, but I would say if you understand the platform like Instagram, you can crack any platform. And yeah, that's my experience. I mean, Instagram and YouTube, I would say if you can crack Instagram and YouTube, I'm confident, especially if you're a young individual, you can crack any platform.
I'd never posted on X much until like two weeks ago. And 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 actually give some value. And that was pretty easy to learn.
And I think if you start on X, it's a bit harder to get into video because video is a whole other beast. Sitting down and filming is not an easy thing. I've had some colleagues, I pushed them to start making videos. Shout out to Eric. He's our media buyer. How to make a video. And yeah, he struggled a little bit in his first month, but I think it's good to step out of your comfort zone and try and film some videos. But yeah, it's definitely not easy. So I would say yes, Instagram and YouTube.
That's actually how I discovered you, on X, and it's just blown up and now my entire feed is just Hector videos recently. So I didn't realize you just started posting in two weeks. That's insane. Clearly another sign of how effective you are at this. So another kind of bullet point I want to double down on there is just this idea of young talent. That's something you talk a lot about. Just the value and almost the alpha in hiring young people.
Yeah. I mean, also going back to the point that you had just mentioned, how it's the hardest role to hire. I think it's very simple. It just boils down to what I mentioned, the two resumes. There's no clear path for a good marketer or good modern marketer who understands socials. And if you look for these things that you might think are high signal, whether it's the best grades, the best school, certain majors, you're not going to end up with the marketer that you had envisioned. So I think that's why it's hard because there's no real defined path of, "Okay, this is how you find the next Togan or the next type three or the next X person."
So yeah, my suggestion if you're trying to find someone similar to me would be try to not find someone similar to me because you're not going to find the right person. It's just give a shout out to some kid who has some crazy background, and the crazier the better, and obviously has some proof in the work. But yeah, the point that you were asking was the importance of young talent, right? And why that really matters.
Yeah.
I think I've seen this example in a lot of different industries. I don't know if you've heard of Jimmy Farley, but he's one of the TikTok Shop OG guys. 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 in-house with them and also with two other brands.
But I've just seen this kid surround himself—I mean he's older than me now, but I've seen him surround himself with all these older founders and all these older founders of these e-com brands are always just talking about how having a Jimmy next to you is 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 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 e-com, whatever it is, and you just find someone that kind of 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 a no-brainer to have someone like that on your team. Even if you do your best now to dive into TikTok Shop or into Trybe, you're still going to struggle because you're not going to be able maybe to connect as much with the creators, or you're not going to understand certain things. And it's just going to take you a lot longer time to get used to those things, instead of putting your time into something that you're better at and then bringing someone that can manage those things for you.
I love this advice. There's always talk about 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.
Yeah. And I think obviously Tanay is super young, and he's one of the smartest people I know. He'll still bring me into his office or hop on a call and be asking me, "What's working on Instagram? How are you doing this so fast?" Or just ask me questions about content in general. I've seen this from Tanay and the team in general. 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 the day you stop growing. And that's something I've definitely learned from Tanay. 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. Yeah.
I love that. And you joined Wispr at 19, right?
Yes, I had just turned 19. It was three days after my birthday.
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.
Yeah, I mean—
Give people some context.
It was a weird transition because I had just quit Division I soccer three days before as well. And I literally went home, looked up Wispr Flow on LinkedIn. Well, I want to say I looked up creator jobs on LinkedIn. I applied to 200 positions, found some company called Wispr Flow. I applied, had a call with Tanay, and then I joined.
It was crazy. Looking back at some of the memories, I remember it was 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 left to go to the bathroom and popped up my laptop, and I hopped into 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 I got out of calculus, and I just started editing a video. I had some editing experience, but for Tanay, on one of my first weeks, to ask me to do that was pretty scary.
But that 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 it probably took me a year to feel actually comfortable. And there were 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 had been a whole school year. And then it was my junior 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. Obviously I was enjoying Wispr, and I was making some decent money from my personal brand, but I was like, "I don't know if this is a real career." And my parents, we immigrated to the US and everything, and me being in college and 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 a finance internship. And two weeks into the internship, I 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'd 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 click. And that's kind of how it worked.
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 thing. I'm going to come back to how you find the creators for this kind of paid UGC strategy.
If we walked through the whole strategy honestly now, I think this would be a good moment to walk through everything. So, like we were mentioning, the first step is figuring out, okay, if you're in SaaS, you're going to do percent of ad spend. If you're in e-commerce, you're going to do percent of GMV. And then from there, you'll set up the group, 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, 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 going to be able to get the best of the best. And this is where a lot of companies go wrong. They'll start doing a lot of outreach on these platforms. Why would a creator want to work for a brand that has no money? For example, on Trybe it says how much money we 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. And 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 that we get. But on the contrary, if you're a brand who has $0 paid out and zero creators, it's going to be really hard to get creators in.
So what I did is I went off platform, and I went on a platform like Instagram. And you just look up a bunch of keywords. It can be UGC creators, tech, nine-to-five, lawyer, doctor, 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. And then you also go through their following and follower list, and you also search those same exact keywords, because typically good creators know other good creators. And then I'd say around 150 to 250 DMs over a week. And these should be very targeted DMs. It shouldn't be like, "Oh, I'm going to use some mass software and send 3,000 messages."
You need to care about the small things, because nowadays with all these automations, yes, you can do a lot of things fast. But if you do it very fast, you're probably going to get a lot of slop back or a lot of bad creators back. And I think for outreach it's still better to do it manually. Obviously it's going to take a bit longer, but if you do it right, I haven't had to do outreach ever again. And from those 150 to 250 DMs, you're probably going to get 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, which is just doing all these events and things for the creators, whether it be meetings. 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. We're hosting a retreat in San Francisco next month. We're flying in some of our best creators from around the world. So these little things that you start to do to build up more and more culture.
And then from there, you have a small group of creators, you've also set up the 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 five to 10, 10 to 15, 15 to 20. We probably added five to six creators every few weeks. And since at this point you also have 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 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'll only accept maybe one or two or three. But we grew pretty slowly, and now we're at 50 creators.
And aside from accepting creators from Trybe, one of the things we've done actually is we've introduced a referral program where we will pay creators $100 per creator they bring into the group. And it's not some sort of MLM pyramid scheme thing. There were a bunch of people on LinkedIn. My post blew up on LinkedIn, and everyone was like, "This sounds like a scam. Sounds like an MLM pyramid or whatever sales." And we're not paying them to just bring creators in. 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. 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." This is a very tight-knit family, and it's just our way of saying thank you for helping us grow the program. And those are some different levers we've applied to 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—
No, I'm good. I do have questions, but keep going.
Yeah, that brings me to the last step, which is now you have the culture, you have the people in the group, you're at a decent size, you have the percent of GMV, percent of ad spend. And now one thing that's going to start to happen is you're getting a lot of ads. And your ads are going to show in the group. It's going to show, "Okay, which is the ad that's doing the most spend, second most spend, the third spend?" And your creators can see these things. And obviously you want them to see it, but it can also backfire if you're not good at coaching your creators. Because these creators will see the top-performing ads and they'll be like, "Okay, I'm going to copy those ads as well. I'm going to 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.
And Meta, when an ad is 160% similar, it ends up grouping it together, whether it's the same T-shirts, you're in the same setting, you're saying the same words. Andromeda is super complex now. And for example, it'll scan your ad five times over, it'll pull the transcript, it'll pull each frame out, it'll look at the text on screen. And if you think about it, nothing's going to get past that. And that's why you can reach ad fatigue really quickly if you're constantly repeating the same formats, the same messaging, the same people.
So what we do is we continuously push these creators and remind them the reason these creators are making so much money and that their ads are all at the top is because they kept experimenting, and they kept leaning into what they were 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 going to rank under them and you're not going to 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, that's why I say the creators sometimes understand the product better than me and come up with better concepts and ideas than me, and that's why I stay away from briefs.
One example of a really good ad that we had recently was this creator had his keyboard outside his window on a roof, and it was raining. So it stops you because it's a very interesting visual hook. And then it pans over, and on the thing it says, "What is my keyboard trying to say?" And it pans over to his laptop, and 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. I don't even know how he came up with that. So kudos to him. But that's what happens when you keep it really open-ended, you have a fun product, and you let the creators have fun and just keep experimenting. And no two ads in our ad library look the same.
Wow, amazing. Okay. Let me try to walk through the steps here because this was so much juicy gold stuff, advice. So step one, sign up on Trybe. Trybe is kind of where you manage creators and pay out and all that kind of stuff. Your advice here is don't work through Trybe to find them because no one's going to care about you yet. And your advice is go to Instagram, keyword search for things in your market, UGC, tech, lawyers that maybe want to make money on the side, to recruit the first five. The advice is start with five, don't go too big. Okay.
And I would also—it's not even just start with five or start with lawyers or whatever. 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 that applies to everything in life. But specifically in creators, if you just bring 100 or 200 of the same creators, that isn't going to lead to scale because, again, everything's going to 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 different creators that can all make net new concepts. And it just exponentially grows the more different creators you bring on board. So it's not just the point about bringing a few creators, it's also being very specific about those few creators you're actually bringing in.
And so when you say that, it's think about what customer, what kind of market, what ICP you're targeting, and what's the creator that will speak to that audience.
Exactly. So at Wispr, we have everything from moms to lawyers. The awesome thing about Wispr is when you have a product that people love, you get so many cool people wanting to work with your brand. We have an eight-figure e-com founder that loves Wispr so much that he just makes ads for us. And I find that pretty incredible. Some dude who has a successful e-com business, he loves Wispr so much he just wants to be part of the community, and he's 45, has kids. And we have basically anything you can imagine: engineers, lawyers, moms, sales reps, agency owners, 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 my brand, or I haven't had success with UGC." And a lot of 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 going to be an older technical person, and you can't get by bringing on an 18-year-old who isn't technical to talk about your
Product. And those ads might look a lot different. For example, our technical ads at Wispr, when you're speaking to this older demographic who isn't really on Instagram that much or 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 a screen recording of someone using your product. It could be a minute, 30 seconds long. It can be super long. Some of our best ads, you would look at them and you'd be like, "Holy cow, these are ugly. These are such bad ads." 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 the same thing for a sleep product. If you have an expensive product in the sleep niche or industry, whatever, and you have an 18-year-old kid selling it, why are you or why am I going to buy a $3,000 product from a kid? Probably it's not going to work that way. You want to buy from someone who maybe speaks the same way you do, who works in the same things you do, has the same problems you do.
And yeah, I think UGC works for any company. It's just the more upstream you go or 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 want to make content about my product?
And this unexpected element of what works is part of the reason I imagine you run so many ads. You mentioned you do 700, 500, 1,000 ads a month. Part of the reason is to discover the ones that are working.
Exactly. Yeah, because ads, I would say, is almost weirder than organic content. I can kind of put my finger on what works on organic, but sometimes I'll see an ad that comes in and 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 such a high bar for, oh, if the ad doesn't work this way or that way, we're not going to run it. Again, some of the ads that I made a year ago, it's literally 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 ones as well.
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What does the DM look like when you reach out to a creator?
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 the number one place I would actually start, and a lot of our early creators came from there. 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 come across a lot of creators. And from there, 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. I would love to have you be part of our creator group."
And I don't necessarily pitch the performance-based thing yet because it's still a relatively new thing for creators, hearing this new model, and a lot of them are skeptical at first, which I understand why. But even seven months ago, six months ago, it was even more new. So even today, I still wouldn't start with that and 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 a PDF that's super simple. I just 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 onboarded in Discord, get them a 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, I'll just send them a DM and be like, "Hey, I have come 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. 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.
And this is from the Wispr Flow Instagram account?
Sometimes I do either or, because since I'm a creator myself, 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." That's one of the cool things about hiring a content creator. If they make, again, content, and you just make sure they make high-value content, they can also be used as a very good hiring mechanism.
And yeah, it depends. If you have someone who's a creator, I think it works pretty well. Obviously you get a creator face, whatever. And then also if you're a really well-known brand, obviously if you're a creator getting a message from Nike or whatever, you know what I mean? It's very impressive, and you're probably more likely to get a response. I think it just depends.
And then, okay, so you DM them, they're interested, you send them kind of an overview. In the early, say the first five, you say you hop on a call pretty quickly and just pitch them and explain the program. What's onboarding look like?
These creators are very used to just being used, and everything they do is a transaction. They make a video, they get paid, and they never talk to a person again. And we live in a day and age where everything is digital, everything's virtual. Most people are working remote, most creators are remote, and they crave community in the same way just like a regular person would crave community. And we just make sure that we connect from the get-go, and at the end they're just friends. We're working together. I don't see them as just, "Hey, a creator that I'm going to extract some videos from and never talk to again."
I get on a call with them, like you said, and I have this whole slideshow. But before I go to my slideshow, I ask them about themselves, how they got into content, why they enjoy it, and just have a conversation. Try to get to know them. And then from there, the flow of the slideshow is I have an intro slide where I talk about myself. I talk about my background as a creator, so they respect me and they know I'm not just some random dude talking to them. 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 let them know what they can expect in terms of the flow from them making the video to it getting accepted to it getting run as an ad. I tell them we pay them out every seven days, which is another hack as well. You want to 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. So yeah, we pay out seven days. We tell them that. 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 a sales deal. You don't want to get them all excited and then you let them get off and then you have to chase them down. You want to be very strategic with your time and their time. So I try to meet them, introduce myself, get them onboarded, and get them going so that they know, "Hey, you can start making a video right now."
So, big lesson here is treat them like humans. Care about them, help them feel like they're part of this thing, not just feel like, okay, you're going to make money. Just shut up, don't worry about it. You're going to make money.
And I think this is actually really good alpha as well. So I think the companies that will win long-term are the companies that have the best relationships with creators because 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, etc., word will get out and creators probably won't want to work with you, or you won't get the best terms, or you won't get the best quality creators. So I think one really big thing we focus on, not even just with creators, but any external agencies or anyone we work with, we always want to treat everyone with a lot of respect. And yeah, I think it's the companies that do that the best will win long-term as well.
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?
Honestly, 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 120 full-time employees now, which is pretty crazy, because I joined, I think we were four at the time. I remember I messaged Tanay the other day. I was at the office and I was like, "Holy cow." I just had a moment where I was like, "There's so many people around. This is crazy," 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 be the comms with creators, come up with new concepts, approve videos, get everything kickstarted, and then you need a media buyer. 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, so I'm happy I don't have to do that. But yeah, we have Eric on the media buying side of things, and he structures our ad account and everything.
So this media buyer, is this kind of like a performance marketing person that just lives in Facebook's ad system, or?
Yeah, exactly. Eric basically just lives on the media buying side of things, on Facebook, LinkedIn, YouTube, etc.
Got it. So you're kind of the creative, you're the content supply, and then this person takes it and then is responsible for running the ads, watching performance, so optimizing the spend. Got it. Okay, and then is there anyone else that you find important, valuable on that team early on and even later on?
Early, if we go back to the early, early days, the marketing team was Daniel, our CMO, Matt, who was our head of growth before Eric came, and then it was me as a sole creator, kind of just making the ads myself. And then we had some external agencies here and there, and then slowly we added on design. We added on an in-house director to produce films and launch videos. Then we introduced PR recently.
And even now, I think we're still pretty lean. I think we might be 15 people on the marketing team full-time. We have a creative partnership lead for influencers. We have a celebrity talent manager that helps us close celebrities and things like that. So even then it's still pretty lean, and everyone is experts in their domain, and it's all very flat. We all just have free rein. We all do what we're best at. There's no really middle management. And then our poor CMO Daniel, who's an absolute legend, he just has a bunch of direct reports. So I feel sorry for his calendar, but yeah, that's kind of how everything is structured. It's very flat. No middle managers. Everyone just does their work.
Is a core 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?
So, are you comparing to what I was doing versus what we're doing now?
When you think paid ads on Facebook, Instagram, TikTok, most people think I create a video promoting my product or create 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.
Yeah. So the way I look at it is I was basically an in-house UGC creator. And it got to a point where ad spend was getting too high, and I'm only human, and I couldn't make that many videos. And it was also getting into a year plus of making ads. So naturally I was getting pretty burnt out being a one-man show, and I was like, "Okay, I have the skill set. I'm a decent creator. I can spot good creators as well. Why not just build a team that's an extension of myself?" And yeah, 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, once you get to a pretty high budget on ads, your ads are typically going to reach fatigue a lot faster. And especially with Andromeda now, ads reach fatigue even a lot faster, because before then, 2024, when we were running ads, I could have an ad running for 12 months. 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, once it hits $100,000 in ad spend, will be dead, and that can be hit in a month or two weeks, three weeks. So we constantly need more output, more volume, etc.
And I think that if you look at our ad library, we might have 5,000 lifetime ads and maybe 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 set or our ad library isn't only full of UGC videos. There's a lot of different things as well. Everything from statics to high celebrity/influencer videos to in-house ads to launch videos that we package as ads to founder-led things. So there's a lot of variety in there, and it's just basically having as many formats as possible, because again, we have a lot of ad spend, and we want—the more variety the better at the end of the day.
Okay. So this is just a core leg to the stool of paid ads, is UGC. Clearly working. Do you think this will work for every company? Is this something most B2B—I don't know. Yeah, do you think this will work?
I think this works for everyone, and it goes back to what I was saying. It's just finding those users that can speak to the users you want to acquire. And at the end of the day, one thing that we look at at Wispr is 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's part of those teams, and maybe you get them as a solo—how do you say, a solo customer or whatever? 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 a deal. And that's realistically how most companies can approach that at the end of the day. And it's not like, "Oh, who from X company is going to watch my video and hop on an enterprise call and want to close or whatever?" But I think if you approach it from, companies are made up of people, and you just look at it like that, and you think, "Okay, how do I want to sell to these people, and how would these people respond well to getting it sold to?" I think you just have to break it down super simply, and you're like, "Oh, yeah, this would work for anyone."
Okay. That makes sense. Also, what I'm hearing, though, is this is probably most effective for product-led growth, bottom-up sort of products. Not like a Workday or a Salesforce. More like a Wispr Flow or Notion and things like that. Awesome. And 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 slash 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, because they're trying to convince them how awesome it...
I also think that a good distinction as well is, I think 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 are seen now as sellouts a lot of the time. And when you see a big face or a big celebrity selling a product, it's like, "Oh my gosh, this person has been selling me things 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 not really knowing who the person is, and they're not famous, they don't have a lot of followers. And if you have these partnership ads coming from their account, it just feels a lot more genuine as well. So just want to throw that out there.
The less they look like an influencer.
Exactly.
The less they look like they're trying to convince you, and they're just talking like a regular human about how awesome your product is. I get why that would work.
What I think about right now is there's that survey that someone did a while ago of just, "What do you want to be when you grow up?" And for young people, it was creator, influencer...
Yeah. I think a lot of people were saying they want to be a streamer or live streamer.
Yeah, versus astronaut or lawyer.
Yeah.
And so 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 a creator online. So 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," or 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?
I think the best advice would be to stop looking for advice. It sounds dumb, but a lot of times I'll have a lot of friends reach out and be like, "Hey, I want to get started." And I've had this happen for maybe the last three years, where people are like, "Hey, I want to get started. I want to start making videos like you." And I hop on a call with them for 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 you're a person who's going to ask before doing, you're probably not going to succeed.
And even the best people—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 specific things that they do to lock back in, whether it's weird noises they make with their mouth, or they fidget with their hands, or they have a phrase they repeat over and over again. Or I've even seen some creators where they start stuttering a lot after they've been doing the same scripts over and over again, and they'll put a pen in their mouth and will open their mouth bigger and talk and enunciate. Is that how you say it? Enunciate the words.
Mhm.
I guess more, and then when they stop and they take the pen out of their mouth, then they were able to pronounce it better. So it's a natural thing as a creator. And even if you're doing this for 5, 10, 15 years, there's going to be moments where you have to cut the video, or you're going to stutter, and you're going to have to refilm for 10 times, and you might cuss out your camera and turn it off. But it's just, turn it back on and keep filming sort of thing. And yeah, that'd be my advice. Just get started and stop looking for more advice, because there's no better way to learn as a creator than just turning on the camera and posting.
I love that advice. And what I'm also hearing is you don't have to—you don't see how much people struggle doing this stuff. You see this polished video, and you don't know they had to put a pen in their mouth for...
Yeah, exactly.
Or cuss out their camera.
Yeah.
Even my video that went kind of viral on X, I think it's, what, a 15-minute cut? I did two cuts before that. It would probably take 30 minutes. And then I did that last one, which is probably again 30 minutes, and then I package it into a nice video. I do this for a living, and I managed our Trybe group for the last seven months, and I know it like the back of my hand or whatever. And even then, I still struggle going through and putting my thoughts concisely and going through everything. It's not perfect, but I put the message out, I gave some value, and people enjoyed it. And yeah, I don't think it needs to be perfect.
That's so great to hear, because watching your video, you're just so chill, so relaxed, just sitting there talking with a little iPad. And people see that and, "I will never be as good at this." So that's really helpful to hear. When I think about starting to create, being a content creator, I feel like I need to get a little fuzzy mic or something. You feel like that's step one.
It's a cannon of a mic.
That's right.
You're not a creator unless you have a tiny fuzzy little mic.
Yeah.
Let me ask you one final question along these lines. Say someone is like, "Amazing, I'm going to do this. We're going to commit to this. We're going to hire. We're going to 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?
I think a lot of the times, 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, I guess, requirements. And you're not going to end up attracting the best people. If you put out an offer where you're going to pay, I don't know, "Oh, these people who are running UGC campaigns are in super high demand. I'm going to put out a job listing for 250K, 200K base salary, generous equity," you're going to end up attracting the wrong type of people.
When I joined Wispr and when Tuan joined Wispr, I can tell you we were earning nowhere near that. We were interns, and we're 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 going to get you the best hire to run this for you, you're in for a rude awakening. And yeah, I would focus on just finding a scrappy kid who's hungry and willing to learn, and you just got a good feeling from them.
I was telling you this the other day as well, our first call. So I had a first call with Julia, which she was leading our marketing team initially when there was four people. And then I had a second call with Tanay. And I remember, mind you, they're hiring me as a UGC creator. I'm 19 years old. I've never worked in a startup. I was not earning much money, and I told Tanay, I was like, "I want equity in Wispr." And Tanay laughed and was like, "I like you, man." And maybe it was a stupid thing to say, but I think it showed how, I don't know, I was naive, but also hungry, and I believe in the company, and I want to be part of the company. And just cues like that, where it's a young, naive, hungry kid who just wants in and wants to learn and wants to grow. And then, yeah, I think, don't want to look in the wrong places, because you're going to attract the wrong people.
You had a couple of awesome tweets along these lines. One is that everyone looking for a marketer with the best resume is going to end up hiring a bot.
Yeah.
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.
Yeah, I think that pretty much sums it up. And also another one that I resonate with a lot that I put out recently was the sports outlook on hiring. Sports teams, I come from a very competitive sports background. I played over in Spain. I played for Real Vigo in La Liga Academy. I played MLS Next in the US. I played Division 1 in college. And we have all these structures for sports teams where you scout young talent, you bring them in, you coach them, you develop them for 10 years. And then if you're over in Spain or over in Europe, you eventually 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, and they join your first team.
And I think a lot of startups should adopt that mentality. 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. And yeah, I think taking a chance on young people and giving them some money to test things with and giving them some freedom to test things with, and allowing them to fail and continue learning, was one of the best models I think you can pick up from sports. And obviously it works. I don't know if you're very familiar with soccer, but look at Lamine Yamal, just won the World Cup at, what, 19 years old, 18 years old. And I think that same approach can be applied to the startup world. Find young talent, invest in them, let them get real reps in the real world, and then eventually they might become one of your A players.
I love that. And I love that also part of this is giving them time to figure it out.
Yeah. 100%.
What's really interesting about this conversation so far, I'm realizing, is I don't think we've once mentioned AI as a part of this work that you do, which is really interesting because 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 what you think with how AI plays into this and how AI should not play into this.
I just think overall, when you look at a lot of the work done, even looking at the top labs, they are some of the people that have the most amount of humans actually working on a specific asset. And maybe, yes, they have a lot of the research automated or a lot of different steps internally automated, but the actual production of the asset, whether it comes to the video, the design in Figma, the editing, the post-production, et cetera, it's all done by teams of a lot of humans. And I think there's not going to be a real way to get around that, at least not anytime soon. And especially in the environment we're in now, where a lot of people are very, I guess, turned off by AI, and it can be a scary 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 the tools to be able to be more productive, to do more work, 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 going to be received really well. And it just looks off. And when I say that, I think it goes more towards not automating the work that's going to be the final product that people are looking at. Because I think you see it a lot of times, it'll end up blowing back on the companies, whether it's an animation that they made with Claude or some sort of asset that they made, and maybe there's typos, or maybe the writing is all jumbled up, like what happens when you do it with ChatGPT or whatever. And yeah, I think it's not worth it. The risk versus reward is not worth it.
So the alpha, what I'm hearing here, is don't use AI for this work.
Yeah, for the final output, especially on the creative side, what other people are going to see, I don't think AI should touch yet.
That is really interesting. It feels like everyone's hearing, lean into AI.
Yeah. Even one of the most bullish people on AI that I know, Matt, who is now at Viktor, or Exited Growth, he has the most automations I've ever seen in the whole wide world. But even then, that last 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 whatever.
And yeah, I think with everyone also just shipping so much volume, whether it be on X, on LinkedIn, on Instagram, on YouTube, you're able now to make videos with Claude, you're able to edit them, you're able to make a doppelganger of yourself with AI and all these different things and get content out faster, and have these automations for tweets, and have it 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 so if you actually have real value, you package it well, and you post not a lot, you post with purpose and for actual reason, you can cut through really easily as a brand or as a company.
I think another good example of this is also Tanay's YouTube channel. We started it around, what, three months ago, and five YouTube videos in, we're millions and millions of views, 20,000 or 21,000 subscribers on YouTube, which is one of the hardest platforms to grow. And a lot of people think, "Oh, we're starting a YouTube channel. We need to post three videos a week." And it's like, no. 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, you get really good end product, and people actually can see the effort you put into it.
That's actually where I was going to go, and this could be our final thread to chat through, is just this other lever, which is, I don't know if you just call this founder-led growth, or—
Yeah, founder-led content.
Founder-led content. Just give us a sense of that growth opportunity, what you're seeing there, the opportunity to drive growth for your product through founder-led content.
Yeah, I think it also ties into what we just talked about: so much AI and so much ads and companies, etc. And at the end of the day, it ties back to everything in content, creator and people. 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 when you compare two products, even from my own experience, if I follow, I don't know, let's say I follow George Heaton, who's the founder of Represent. He has a clothing brand. And then there's another ad that I see for a clothing brand, I'm much more going to buy 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. I know how hard he works for his company and what he actually puts into it. And I think people really appreciate that, and again, such a digital age, being able to connect with the founder behind the product.
And you not only create superfans and people who already use your product but now also love you. You also bring in 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 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 this long-horizon type play, this 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 going to switch off and be like, "Okay, I don't want to 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 what the culture is like, what you're building, people really appreciate that, and you get them to buy in and drop their guards. And then maybe a year in, we actually maybe have a soft sell, or maybe we have to have, "Hey guys, here's some support. Thanks for getting us 100,000 subscribers. Just want to drop this code. Blah blah." And then people are going to want to support you.
So I think, again, in this world where everyone's just trying to get instant growth and everything's super fast and optimize everything from the start, these 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.
What are some of the angles slash 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?
Yeah.
Is there anything there?
So the way we thought about it at Wispr, at honestly any company, is every company is going to have some sort of story or some sort of mission that they're building towards. For us at Wispr, it's getting to one billion daily active users. And 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 going to be different, but it all ties back into the overarching theme.
And whether you're, again, building in medicine or dev tools or whatever it is, there's going to be some sort of mission that you're chasing as a company. And you want to bring people along for that ride. And if you tie that into every episode or into every LinkedIn post, every X post, obviously the formatting and the messaging is different on every platform, but if you tie all of this together, it brings everyone along 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 vision, this is what we're building towards, and this is how each step actually leads us to that." It's our mission. It's almost like a physical representation of a product roadmap or what's actually happening to the company, showing it on display to the world, the ups, the downs, the struggles, everything. That's how we think about it at Wispr, and how I think other companies should think about it as well.
That's awesome advice. Basically, have a North Star metric that you're chasing.
Yeah. And the journey there, and things you're learning.
Things that are surprising. And we'll point people to the channel to give them a sense of what you're actually doing there.
Yeah, it's just Tanay Kothari, and we just document everything on there, the episodes. We've basically done everything from showing how we launched our new product, notetaker, to Tanay going to India and doing wedding shopping, and also working remote and how he balances that and his relationship with Sahaj, to just a week in the life of a founder. We also did a whiteboard breakdown where I spoke with Tanay. And it's all these different formats that all might feel different and look different, but they end up building towards this bigger vision of what Wispr's building towards.
I imagine there's already some innate interest in Wispr Flow when you started it. It's a company people, when they see it, they're like, "Oh, I want to." So there's probably a bit of, you can't start that from the beginning when no one cares what you've learned because no one cares about your company yet.
I honestly think you can start it, though. But maybe it put us in a bit better of a position. But there's founders who don't have brands as big as Wispr who have found success with personal brand content. And again, it's a gateway into the actual brand. And it's like, what easier way to make that accessible than through a person who's just telling their story and getting value?
And so interestingly, this is just another, let's say, alpha opportunity to grow, which is the founder sharing their story in a really compelling way.
And you see everything starts to tie in as well because the more places you show up organically and the more touchpoints you have with the customer, the cheaper it's going to get when it comes to paid because, what is it? I think a person needs to see a piece of content of a company seven times before they actually make a purchase. If you're able to hit them on YouTube long form, which is a bunch of trust built up since it's a long-form platform, and then you're also posting Instagram Reels from the founder, you're also posting on LinkedIn, then when they get to the first ad they see, they're going to convert.
So I think these organic channels work hand in hand with paid. The more that you have activated and the more you have running, the cheaper all the conversions get across all platforms.
And then your paid platform gets credit for that conversion.
Exactly.
A final thing I just want to talk through briefly. You had this awesome video where you share what the team looks like to do founder-led content. I'll briefly share because I think this is really important for people. I will point to the video where you go deeper. Basically, it's a head of content, a videographer to film you, a YouTube team to package it, and short-form editor to take it and create clips.
Yes, exactly.
The content person, would that be you? Are you that person also doing the UGC paid stuff?
Yeah. So I'm the head of content, and that's why if you find a young person who understands content, they can basically do anything, whether it's organic, whether it's paid. And that's why it's important to find someone with a following as well because, again, I understand how to build a following, and I know how to build a team now. And the funny thing is, how I was mentioning previously, every person that's part of my team, whether it be for UGC or whether it be for the founder-led content team, I hired them from my Instagram stories.
The way I got our videographer, he's 24 years old. I posted on my Instagram story, I think it was in May, right after my college graduation. I posted, "Looking for a videographer full-time in San Francisco. Slide up if you're the right fit." I probably had, I don't know, 80 people reply on my story. And then from there, there was this kid named Alex. He was in Australia at the time. He was an American vacationing in Australia. And he seemed like a great fit, and we flew him out to San Francisco on three-day notice, and we got him started. And then same for the YouTube agency. We met through Instagram, and now they're some of my close friends. So it's like, typically the best social people you also find on social platforms. Sort of how it goes.
There's just so much win from having an audience. It's a win we're going to take away from that.
Yeah.
One hundred percent.
From your story. 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 YouTube team, short form. You actually shared the YouTube packaging team, if you had to pick which needs to be stronger, you found the YouTube team is more important than even the quality of the video.
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. 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.
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 going to 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 going to rank the highest, you're not going to get the results you want.
And that's why I think the YouTube side is so important because it's not only a thumbnail, it's not only the click-through rate, it's not only the title, the watch or the average view duration. It's also the storytelling, the pacing, how you package it, the intro, how the thumbnail needs to tie into the video, and there actually needs to be some sort of payoff because if you don't, then you're going to have more of a drop-off rate, and people aren't going to stick along to actually watch the video.
And 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, I guess they're not as committed because they typically have a lot of clients, and they're overseas as well. A lot of our short-form editors are from Germany. 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, want to get a lot of clips out. So they're not going to pay as much attention to the actual storytelling. They're not going to 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 cut a super good video, then I can send that to my editors in a clean slate with no titles, no music, etc. And they can just cut the best moments and make it into really good short-form pieces. And that's the reason why I say the long-form team is the most important part. And it's also the one that has the most legs. YouTube videos can run on for ages and ages.
Even on my own personal channel, I've had a video that's been up now for five years. And I think a year ago, it was at, what, 40,000 views. Now it's 600,000 views. And YouTube videos have the longest half-life out of any platform, and it's truly insane. Some of the videos we post on Tanay's channel might be five, six million views in a few years. And that's what's cool about YouTube. It's a long-term investment.
I've discovered very similar things with YouTube. It's a wondrous platform. It's maybe the only platform where new people discover you at scale.
Yeah, it's insane. And a lot of these platforms, trust me, I enjoy making content, but sometimes it's a bit demotivating when it's like, "Oh, you filmed one piece of content, you posted it. You got to 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 where you post a video and in 48 hours it's dead. A YouTube video, you put a lot of effort into it, and we look at some of the charts on Tanay's videos, and we're still getting 10,000 views in the last 48 hours, even though it's been three months since it's been posted. It's still working for us. It's still getting new eyeballs and new customers. So yeah, YouTube is amazing. I assume also with how many podcasts you have as well, the amount of views you're getting from years and years back or whatever is pretty insane.
Yeah, it's fun to watch videos that have climbed the ranks over time. I had 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 approaching number one. And so you think these are stuck at that number, but they just keep going, going. It's like this, and all of a sudden it just goes like this, and you're like, "Oh, I did not expect that." I don't get a lot of those where it's just inflecting, but it does grow, and it's like, "Wow, I did not know that was still growing."
Yeah.
Anyway, Hector, this was incredible. Before we get to our very exciting lightning round, is there anything else that you want to share or anything else you want to double down on and leave listeners with?
I guess my last point, which I mentioned a lot, is I would just urge other founders out there, give a chance to young talent. And just find those people, believe in them, trust in them, give them opportunities. And not only will they turn into some of your best A players, but also the amount of loyalty they will have to you is quite incredible. And whether they stay at your company or they go on to do other things, they will always be there to help you or help you bring in other young talent or guide you in the right direction when things, when not new alphas out there.
And I'm super grateful to Tanay and Daniel and the whole Wispr team for taking a shot on me. And there's no better place I think I could have landed, and I'm forever in debt, or however you should say that, but I'm just super grateful for the opportunity I was given.
That's beautiful.
Well, with that we've reached our very exciting lightning round. I've got five questions for you. Are you ready?
I've seen these. I've seen these in the podcast. Won't be a surprise.
Okay, here we go. First question, what are two or three books that you find yourself recommending most to other people?
I'm going to give one book. I'm going to give one really good book, which might be a cliché one, but The Almanack of Naval Ravikant. I remember reading that about two years ago, or maybe a year and a half ago. It was kind of in this moment where I was sure I wanted to do content, but I also didn't understand why it was important or why it mattered so much. I read it the first time, didn't really make that much sense to me.
And then I gave it some time, and then things started to line up like it said in the book. How does he say it? Media is one of the best forms of leverage because you don't have to ask for permission. It's permissionless leverage, and you can just make stuff and put it out on the internet, and it will continue to work for you.
I started to see that compounding effect over time of me putting myself out there, and it's a book I continue to find myself coming back to and reading. I bought it for my little brother as well recently. It's something I'm always sharing with friends and always passing on to them to read as well. I feel like it gives direction a lot to young people as well in this crazy world that we live in. So I'd say that's one of my favorite books I've read.
Yeah, and Naval went through this era of just sharing this profound advice on Twitter, and then he kind of slowed down. I love that there's a book that collects it all. I love that so much of his advice, too, you see it and you're like, yeah, it's fine, and then you think back to, wow, he was so damn right.
Have you read, what's it, Ego Is the Enemy?
Is that a book, or is that one of his lines?
No, it's a new book. I think it's called something like that. I was just wondering if you read it because I was interested in reading it. I was about to buy it. I need to go to a bookstore. It's not the only bookstore in Puerto Rico. But yeah, I'm looking for a new book, so if anyone wants to drop some comments on the video.
Okay. Does Amazon deliver to Puerto Rico?
Yes, but it takes a while. Living on an island, everything is a lot slower. Less dopamine rush. You don't get 24-hour delivery.
I love that. Okay, next question. Do you have a favorite recent movie or TV show you have really enjoyed?
I just watched the Elizabeth Holmes movie with my girlfriend. Yeah, I'm not going to spoil it, but wow. It was a really good movie.
One thing that someone shared from the trailer, this is no spoiler. You know that trailer when they're kind of staring at each other, and he kind of puts his tongue in his mouth, like his mouth is kind of doing something funny?
Yeah.
Turns out when he's trying not to laugh or just break character, he puts his tongue against his molars and just presses against them to keep himself from laughing. How about that?
I did not know that. Yeah, but it was a good movie. I liked it.
Epic. All right, next question. Favorite slash most interesting AI product you're using right now, ideally not Wispr Flow.
Honestly, I commented on your post the other day, Miso. Did you end up downloading it or not?
I just tried to check it out. It's a travel tool, right?
Yeah, it's a travel agent, and I travel a lot. I think I have like 55 flights or 60 so far this year.
Jeez.
Like 89,000 miles. Traveling is always something I'm not looking forward to because it gets pretty tiring having to book the flights and everything. I recently came across this product when they launched on X, and I DM'd the founders on Instagram, and I was like, "Yo, get me off the waitlist. I want to try this out." Ever since I downloaded it, it's now been like three months, I can't stop using it and recommending it to friends.
Just an example, the other day I slept through my alarm, and I missed my flight to SF from PR. I woke up, I texted Miso. I was like, "Hey, I missed my flight. Can you get me on the next one?" And I didn't have to do anything else. It took care of everything, booked me on the next flight in like two hours. I just chilled, didn't have to pay anything extra. Yeah, it's the best travel agent I've tried before. Obviously Instinct is a good agent and everything, but I don't think for travel it's anywhere as fast.
And then what's also cool about Miso is they have humans on the back end that will escalate things. If the agent gets stuck, they have direct connections to every major airline and everything, and they can escalate things and take care of it for you. So it's a lifesaver. I can just text and say, "Hey, I want a flight." And it knows, and it'll just send it to me, and I'll get it booked in like two minutes.
That is extremely cool. I looked it up. It's just miso.com?
Yeah.
Miso.com. What an amazing domain. I imagine no affiliation. You're just a fan.
Yeah, no affiliation.
So cool. Okay, go Miso. Okay, two more questions. Do you have a favorite life motto that you often come back to in work or in life?
Yes, I have a life motto that I like a lot. I don't know if I'm going to butcher this, so maybe you can help me. It's from Steve Jobs, that you can't always connect the dots looking forward, but you can always connect them looking backwards.
And when I look into my own life, I see that basically in everything. I was never the smartest kid in school. My parents were always pretty frustrated with me. I had really bad ADHD. Soccer was the only thing I had, and then I lost it, and then I was lost for a few months, even though I was at Wispr. I didn't really understand all the things that were happening or why I even picked up a camera when I was 16, or why I started posting on YouTube, or why I played sports.
And now looking back, everything is so clear, makes so much sense, and I understand the path I'm on in life. I think sometimes you just got to keep going, and then it'll all make sense at the end. Yeah, I think that's one of my favorite quotes I look back on.
I also find that to be very true, and Steve Jobs nailed it again. Hector, this was incredible. Thank you so much for sharing so much. You're awesome. Final question, how can listeners be useful to you?
If you guys want to follow me on X or on Instagram or YouTube, whatever you guys want. Come and join the journey.
And your handle is just Hector Serrano? Serrano.
Yeah, it's pretty similar across platforms. It's like Hector Serrano. You'll find me one way or another, but yeah.
Hector, thank you so much for being here.
Thank you. Thank you.
Everyone, thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.
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