Howie: The AI Secretary | Austin Petersmith, Co-founder and CEO

22:04It was like, these are constraints that are built into the system that we need to work with. and so acknowledging that and then acknowledging that we have chosen space where the mistake tolerance is really low made us start to realize okay what we actually need to do is just pull forward the best possible product experience and then chip away as we go at getting closer and closer to the models being able to do that and then as we do that we can also like give the humans a more complex task and so we can always have a product experience that is far ahead of what the models at a given time are capable of and that will allow us to like get better at training the models, get better at doing the actual product experience and then move faster in terms of like taking on new types of tasks that are beyond what we've originally kind of set out to do.

22:53So once we had that clarity, it still was scary. Like nobody, software people don't like operationalizing a human team. We have 65 people now, full-time contractors that work around the clock that are the humans in the loop behind Howie. And that has been hard, like in terms of recruiting the people, onboarding them and managing them. We have three people on our team right now are at an offsite just planning like the actual onboarding for like the next cohort of people that we're bringing on and the documentation. And like they've created simulated environments for people to like practice and all these different things that just, it's like we've ended up building all of our engineering, most of our engineering time goes to building this product that the humans use so that we can create make them incredibly efficient and incredibly accurate at these tasks and that was like daunting and we knew that if we went down this path that's what we'd have to do and so it was a tough decision it's capital it's time it's energy it's like we have to deal with human challenges that are totally different from the software challenges and and so we have two different layers of the challenges in terms of getting the thing right.

24:04But it was so clear that it would allow us to pull forward a better product experience than was possible today. And that was really important because we wanted to serve the customers at the top of the market who are people that really actually need a full-time executive assistant. And we want to be as good at managing their calendar as a full-time executive assistant. And to do that, we just had to find ways to fill in the gaps where the models weren't capable. And we had the capital to do it. And that's why you raise venture capital is to be able to take risk. And we started to see no one else is doing this.

24:37We inevitably are going to have competitors. It might be two kids in YC that are probably smarter than us, definitely don't have kids, so they can work around the clock and so they can work more than us. And so what do we have that they don't have? And one thing is we We actually can operationalize this. We have the capital to do it. We have managed big teams and we know how to do it. And we know how to build the software tools at scale for them to use. And so suddenly it felt like, okay, if it's right that that is the path to do this, then us doing it now makes us much more defensible, actually.

25:10And that has really played out well for us so far, where we've just been growing pretty quickly since the moment we made that decision back in January.

25:19Turner Novak:Oh, really? I didn't realize it changed the growth trajectory. Yeah. We last year, I mean, we were waitlist only, so we were kind of constraining the growth, but churn was a big challenge and usage retention. Like we had people who weren't churning, but also weren't using the product that much. And from January, it was like the last two weeks of December over Christmas that Dave and I, mostly Dave really actually rebuilt this, the entire kind of system to support the humans in the loop. And in January, we onboarded one customer. And it was a customer who was happy with the old product, but it was not working well enough for him.

25:57His name is Diego Oppenheimer. He's awesome and has since become a friend. I didn't know him at the time. And we said, we're not going to add any more customers to this until Diego is happy. And we saw his usage just skyrocket. So it's like he was telling us that he liked the product in December. and but it wasn't until he had a better experience that he realized how much more he could get out of it where it's like he was just subconsciously narrowing what he would trust Howie with and suddenly was like I can it can fully manage my calendar and and so he leaned into it so hard and then yeah and then since then like it's really just been I mean yeah been a steady clip of like 30 to 50 percent month over month growth and that's been totally just the word of mouth from customers talking about how great the experience is and then similarly like with the retention like the downout ratio has been 30 to 40 percent all year which is just for an early stage product like ours is just really good to see in terms of how often people are actually using the thing and and so that's really exciting because sometimes the the mrr and the new customers can can be harder it's like a lot people will come in and try anything basically and so like seeing that they actually end up using it every single day is just really, really cool to see.

27:13Turner Novak:Yeah, when you said Dow mouse, you said 30, 40%. So what is that like two or three days a week? Basically, what that tells you is that on a given day, of all the people who, of all the monthly active users, all the people that used it in the last 30 days, 30 to 40 % of them used it that day. And every day, that's true. So today, 30 to 40 % of the people who used Howie in the last 30 days have used it today and that will be true tomorrow and the next day and and so for a lot of products where that that can be just a red a red flag where you see it's like lots of people are interested in it lots of people might throw in their credit card but the dao mao is 10 which just means most people the vast majority of people are just not using it every single day which maybe means you have a useful thing with a less frequent use case or maybe means they find it kind of interesting but not actually like that useful or maybe they're all just turning out really fast and then i think doesn't waymo kind of classically had this like human in the loo model forever and they still they still might i don't actually i don't actually know yeah so they do a lot of different things so actually cruise was really the one where and i mean we yeah because cruise was doing this kind of for a long time where we got to know lots of people there in sf back in the day where Waymo was a little bit more quiet about it, but both of them.

28:32And yeah, I mean, the model, like anyone who lived in SF over the past decade, you saw self-driving cars driving around in the streets with sensors on the roof, but there was a person behind the wheel, and then another person on a laptop in the front seat, and the two people in the car.

28:51Turner Novak:In a self-driving car doable, yeah. Yeah, so it's like, yes, it's not a self-driving car. They were just teaching the cars how to drive, And then they do that at a much larger scale in simulated environments where they have people in the Philippines who are in these environments. And what they're doing is creating really structured training data, finding where the models... Because when the human is driving the car, the model and the sensors are still trying to predict what to do. And they can cross-reference that with what the human actually did. And then they figure out, okay, here's a scenario where our models are predicting to do this, and we actually need to do that.

29:25and it helps kind of guide them toward the right answer. And so that has been kind of an inspiration for how we do this. And same thing, it's like today, the vast majority of interactions, we want the human to spot check because we just don't want to make a mistake. Even though most of those, the thing is right. So it's like they don't have to correct anything, but it's worth the quick once over. Over time, we will give more to autopilot. So like the very first self-driving cars that I ever saw were in San Francisco in the Sunset District. And it was like a four block radius in the Sunset where it's a perfect grid.

30:02And they had mapped every inch of the thing. And they had no human in the car and it could drive. But it was a four block radius. And then it was like the whole Sunset District. And then it was the whole city of San Francisco. And now it's like all the way down the peninsula and all over the place. You can get the airport now. Yeah, exactly. At the airport. But if you see a Waymo on an icy road in Lake Tahoe, then there's going to be somebody sitting there holding the steering wheel because they're still training that. And so it's kind of a similar thing for us where it's like we can always push out to something that is harder than the technology can do at a given time and have a human holding the steering wheel.

30:40And we can give more and more to the models to kind of keep taking those things on. And that gives us a really nice kind of like innovation pipeline.

30:47Turner Novak:Yeah, it's kind of interesting when you think about balancing that. Like there's probably other cases where I don't know, I'm just making this up, like logistics, you know, emailing copilot type thing or like like different industries where you kind of see there's a lot of these agents. But really, should it just be like superpowered humans? Like I feel like there's like this weird almost trade off of like people trying to make it pure software where in reality should be like software superpowered or supercharged human. And I don't know. I don't know where the trade-off is on that, but. Yeah, I mean, it's like, yeah, like you see it with employees and companies that are the ones who are using AI effectively are able to just be unbelievably productive to an unprecedented degree.

31:36And so it makes sense that it's like, can you build a fully autonomous AI accounting firm today? Probably not. But could you build like a suite of tools that allow good accountants to be insanely highly leveraged so they can be 100 times more productive than they would have been before because a ton of work is happening for them, but you build the tools so they can have oversight of the actions that are taking place. And so they don't have to spend any of their time on the tedious stuff, but they still are actually accountable for the work because they're fully in the loop and seeing it. And to me, that's a pretty exciting area in general.

32:16and I wish there were more people doing it. And again, software people don't love to staff up a human workforce. And so everyone is kind of trying to build the fully AI accounting firm instead of the highly leveraged tech-first AI accounting firm that has phenomenal accountants that work really efficiently.

32:36Turner Novak:Well, I feel like we almost have this graveyard of people that have kind of tried to do these in the past, like pre-LLMs that haven't worked. So there's almost like a negative connotation, but I don't know. I mean, I feel like we're just going to keep, we're going to keep trying and eventually someone will crack it. Yeah, my last company I used, Atrium, which was Justin Kahn's law firm that was, and that was kind of their pitch was like, we're building, we're getting tier one lawyers and we're building technology to streamline them and the company didn't work out. And I have wondered like, if they had just stuck with it, like they suddenly would have been able to actually streamline these lawyers to like a crazy degree.

33:14and they didn't miss it by that much. It was, I think, 2019 that I was using them or something like that. And a few more years maybe could have totally changed it because legal is definitely one of the areas where AI has become really, really valuable kind of across the stack really quickly because it's just words and the models are pretty good at words. And so, yeah, I do think there's probably going to be a lot of like, I mean, and even Howie, It's like there were previous attempts to build our same product 10 years ago. I mean, the Slack one that we talked about, but even specifically like the email based scheduling X.ai was doing this.

33:50And and so I think there are a lot of ideas that have been attempted in the past that suddenly are like super viable today.

33:59Turner Novak:So you think that thing you've kind of cracked just to make sure I get this right is with the way that the kind of the how the product works, you're making a prediction on what you think needs to happen. and then the humans come in and at the end, those edge cases, they say they do actually follow the prediction or they do something else. And then you look at where the deviation is and you say, okay, we need to figure out how do we make the models to actually match what the human actually did. And then that's kind of how you're tweaking and fine tuning these things at the edges to keep solving these edge cases that don't quite fully automate yet.

34:31Yeah, but you can think about it more like a log of work because the predictions are, there's a bunch of them. So it might be like, we're querying this person's calendar and that person's calendar for these dates on this time zone. And then we're creating this calendar event and this calendar event. And we're updating the user's preferences with this because they said, I no longer want to take meetings on Tuesday. And we're replying all with this message to say that we've scheduled the meeting, but we're also replying to the customer to say, hey, you told me to schedule it at this time, but also you have a flight an hour later.

35:00And so we just want like, so just let me know if like we need to actually move it or something. So there's like all of those could be predictions that then by the time a human is in the loop looking at it, they're able to kind of like evaluate, was this the correct set of steps or if there's a mistake, was it at the very top or toward the bottom and is it something I can just quickly tweak or do we need to like rerun this simulation with some new feedback and yeah.

35:23Turner Novak:Makes sense. Yeah, I'm excited to see now that you guys are kind of, we can talk about the launch in a second, but yeah, now that you're like, you're out there, people know you exist. I'm interested to see who can borrow in different categories. Yeah, totally. And we're kind of laying it out there. I mean, there's tons that makes this really, really hard to build, which is why we don't really mind kind of talking about it. But yeah, and I mean, that is like an oversimplification of it. But I do really think that this architecture makes a lot of sense. And I think that I won't be surprised if competitors of ours start to move in this direction.

35:59But it's also hard. If you are open AI and you're trying to roll a product out to a million people on day one, then can you actually staff up a human workforce? Or do you need to just focus on the use cases that you think the models can do to a level of accuracy that solved the problem on day one? Yeah.

36:18Turner Novak:And so really quick, just before we forget about this, I wanted to ask you the name, Howie. Bold name, easy to remember. How did you come up with the name initially when you started everything? Yeah, so we talked about, Dave and I kind of, we knew we wanted a human name because we had talked to lots of potential customers and we knew that the idea of how we kind of presenting as a human made a ton of sense. And we wanted the company name to match that so that it's not like we're building two brands at once of like this company name and then the assistant name. And so that was very clear, which is interesting because most of our competitors have gone totally different directions without giving these things a human name.

37:02But then there's Siri and Alexa and plenty of precedent there. We knew we wanted a name that felt friendly, which is kind of ambiguous, but kind of when you see it. And we wanted a name where if somebody mentions it in a conversation, then the other person who heard it can actually spell it correctly when they go type it into Google. And we wanted two syllables. We wanted to make sure the.ai domain was available. And we also were checking for the.com to at least, like, we weren't going to buy the.com on day one, but we wanted to make sure it wasn't, like, some, like, a domain that had been actively in use for many years and was, like, would never be gettable if we did decide we want it.

37:45And a couple of others, I guess we weren't totally sure on gender, but we did feel like a male name kind of would be cool just because so many of these virtual assistants with names have had female names. And it's like, why not kind of switch it up? And as we've gone with like secretary as our branding, that also kind of helps because some people did find the secretary thing to be kind of a callback to an era that we don't necessarily want to go back to. But it's like, well, Howie's also a male name. And also we're building this so that you don't have to have the 1950s secretaries. And so a male name works really well in that way.

38:25And yeah, it's just memorable. We had a bunch of parameters. We were building this list of names that kind of fit those. And then Dave sent me this meme that is about a guy named Howie Do It. And it's like a screenshot of his Facebook profile with the Montel Jordan song, This Is How We Do It, playing in the background. And immediately that was at the top of our list. We're just like, that makes so much sense. And so we got Howie.ai. Now we have Howie.com. And now Howie has been seen by hundreds of thousands of people and scheduled tons and tons of meetings. and so everyone in Silicon Valley knows Howie now.

39:04Turner Novak:Yeah, I'm looking at, is it this guy? He's almost like, it's like a selfie in a truck. He's got sunglasses and like a white beater on, like a black beater. Yep, Howie do it, yeah. I'll throw it up on the screen so people can see it. I'll throw a link in the show notes. There's a lot of videos here. People make a lot of videos about this one. Yeah, yeah. That's awesome. And then, so we mentioned, so you launched. You guys kind of like, I mean, you weren't really in stealth because people were using it. You were talking about it, but you did like the, you know, the canonical launch video, which is actually pretty cool.

39:40Turner Novak:So maybe talk about what all went into that. We had not like announced our seed round. So we wanted to kind of do that. We also had for the longest time we had, we had a website that we built, a homepage that we built in like three days really early on. And we had not updated it at all. and it had like maybe 10 words on it total. It was like Howie is an email-based scheduling assistant, I think, and a couple of other words beyond that. But it was like, didn't have much in terms of like social proof. We have all these customers who want to talk about how much they love Howie. It didn't have much branding that was firm in any way.

40:16It was just kind of, I don't know, it was nice enough and it worked, but there was that. And then we had had a wait list for the longest time and we wanted to actually go to general availability so anyone can sign up and use Howie. And so all of those ended up being kind of the things that we launched was we announced the funding, we rolled out a new brand that we worked really hard on that we think will kind of carry us into the next era of the company. And we rolled out general availability. We still don't have like a free trial option. So you have to pay to use the product. But because that filtering has just like always worked really well for us.

40:51So far, everyone who's ever used Howie has paid upfront to do it. And it's obviously like we could optimize more for growth over time with free trials and freemium and all those things. But it's been great to filter to the people that really need this product. And so we've been working on the website and the brand for a while and getting ready to roll that out. And then as we were getting closer to the launch, I was like, okay, we probably have to do a launch video if we're going to do this. We've put so much energy into the product and the brand and the customer stories that a video is going to be the way that we actually make it pop.

41:26And so the launch, we were planning for September 22nd. And I think it was like September 5th. So we worked with an agency called New Kid that's in Toronto. They're awesome. They did our brand and our website and everything. And they're the best. And I think it was like September 5th that I texted Matt at New Kid. And I was like, I think we should do a video. Can you work on this with me? and he turned around like in a day this this like presentation that they did for us of like 10 different ideas for videos literally 10 different completely different ideas all across the board one was like something with the we get montel jordan to do the this is how we do it and and a bunch of different ideas and but one of them was the return of the secretary because we had already gone with we the home page was already saying how he's the people's secretary And so we already were leaning into that.

42:15And the reason for that is there are 10 ,000 assistants in the world and every AI product is called assistant or copilot. And secretary is a word that more accurately describes how he does because it's like administrative tasks like scheduling, not everything that an executive assistant does, which could be more kind of chief of staff type level things. and it's a word that everybody in the world knows and no other company was using. And so we could just lean into it and own it. So we knew we wanted to do that. And so then the return to the secretary video made sense to just lean in harder to it.

42:49And so by, I think September 12th or 11th was the day that we signed the contract. So basically we were like, we want to do this concept. And so then Matt was like, okay, I know a production house and we'll talk to them and we'll see. And so they had like, we had very little time. I think that normally these things take a bunch more time than this. But anyway, so they, it was like, they had a director in mind. The director already had an idea for an actress to play the secretary, which was super helpful because like the casting call part of this would be like one of the most time consuming pieces.

43:22And they, so they had her really quickly send like a self tape of her herself reading the lines and we thought she was fantastic. And so that was the really key piece. But then ultimately it was like 10 days before launch that we signed the contract to do it. And so then like three days later, they shot it. They had to lock down the location and everything. They found a great location in Toronto. And then we got delivery of the final video, I think, like the night before the launch. So it was all like a kind of frantic race to make it happen. But they totally delivered. Everyone delivered. And yeah, and it went really great.

43:56So we were very happy with it.

43:57Turner Novak:What was the name of the firm you said you work for to do that, though? We'll just give them a quick shout out. Yes, newkid.services. Newkid.services. Okay, cool. I'll throw a link in the show notes if people want to check that out. I want to, maybe what we'll do, I'll do a screen share and we'll watch it.

44:19Turner Novak:It's time to bring back the secretary. What? Hold on. Hear me out.

44:28We're bringing back the secretary. Not the job title. Not the dress code. None of that 1950s bold. Hello? But the poise. Precision.

44:38Turner Novak:The prestige.

44:42Someone else is managing my calendar? You get a secretary! You get a secretary! No, I don't have a pen. I have a pencil. No more triple bookings or battling for bio breaks. We're not scheduling meetings to schedule meetings about meetings that are soon to be scheduled. Hi, I'm calling about the meeting for the meeting. Thanks for setting the meeting. It's a secretary for all of us. Yeah. Even secretaries. Meet Howie, the return of the secretary. Things got a little crazy back there, didn't they?

45:13Turner Novak:I loved it because it's just so... I feel like a lot of the launch videos you kind of see right now, they're like... I don't know. How would you describe the current meta of launch videos? I don't know. I mean, there's been a lot of different ones. And like, I think that we wanted something that felt tied to the brand and to the product. We didn't, we didn't feel like it needed to be like a whole kind of like product rundown. Cause that is like one category of product launch videos is just like you talk about the product and we felt like we want people to come check out the homepage. And so it's okay if they're left with questions about, okay, I just, that video is funny, but what is this?

45:55And so we wanted it to be connected to the brand and to the product experience, but we didn't feel like we needed to sell the features in the video. And I think we did a good job of that. I mean, in terms of like, we got about 1.2 million views on the video across the different posts that we had. And it converted to a ton of customers and a ton of revenue. So we were like really happy with that conversion. Like it would have been great if it got 10 million views. but in terms of like how did it like it blew our expectations out of the water in terms of customer growth and so that was great and so i think it did a good job of teasing it and then and it was just interesting enough that you go check out the website and then you get to see like tons of customer testimonials and and we talk about the product more specifically in lots of ways there and have a brand that we're really proud of there and so yeah so i i think that i don't know the other videos i'm trying to think of other ones i mean Like, Cluey, obviously, is, like, completely crushing it.

46:53And I love their videos. I don't know how well they do in terms of converting, but I think that I'm guessing that they probably do pretty well. And then there's, like, the Friend launch, which, like, is mega viral, like, on a scale beyond anything that, like, yeah, at least an order of magnitude bigger than ours. Does it sell the product? I'm not totally sure. And so that was really important to us, that we actually like focus it on the business and not like just getting the views for the sake of the views. And what else? I don't know. I mean, we introduced a character. Some people do these like high production videos, but it's like kind of just the founder talking about their thing.

47:34But we felt like it was cool to introduce a character who we now might end up using as kind of a recurring character in some other videos potentially. And so that idea was fun. And I don't know. Yeah, I think that like for what I was most happy with is that it was a very short turnaround time and we produced something that feels really, really polished. They had a few different inspirations, but one of them was the, I don't know what you call them, but the cutaway videos in the big short where they would do a short anecdote. And I can't remember what they are specifically, but they're these quick cuts and cool camera movements and the idea was just like super fast pace and really high velocity.

48:22And the actress that we used was just so good. She had like her energy. When you, what I was envisioning from the script and all the ideas, this was way less energy than what she ended up bringing to the table. So it's like, just the energy was just phenomenal. And so anyway, I'm really happy with it. And I'm happy that it converted to customers because obviously if it just flopped all together, that would be the worst thing. But also if it went viral but didn't convert to customers, then it's like, was it worth the energy we put into it? And so we're just thrilled that it led to a huge increase in our customer base and tons of new people who now in the couple weeks since have been giving us tons of feedback and loving the product.

49:02And the signups are still rolling in. So that's been really cool.

49:07Turner Novak:Yeah, it's kind of interesting in the sense of like everyone kind of knows what a secretary is or like an executive assistant. so you don't necessarily like to your point about how some people like demo the product like if you just say like hey it's a secretary like it's an executive assistant you're like oh yeah i know what that is and then i feel like the biggest question is okay but it's ai like does it actually work right like i've used all these tools they're all kind of sus so the so it's like go to the website and it's like oh there's just a bunch of customer testimonials about how how well it works so it's like all right cool i'll try it out so it's like an interesting like I think it's almost like you need to position your marketing depending on how mature a category is or like how well the buyer understands and then like what their questions probably are based on like you give them some general awareness like all right what's their next step in terms of discovery is it like do more research is it just like convert immediately is it like they need some social proof do they need like know the price etc so yeah totally yeah I think that like the social proof is just, I mean, for anything, I think social proof is really key.

50:12And we are excited that we have so many awesome people that, I mean, we had like way more than we even could include customers who just were like thrilled to provide testimonials. And so that's been really awesome. And I think that, yeah, just, it's like, ultimately the, our job is to just get people interested enough that they have an idea what it is. And then the customer testimonials do the heavy lifting of like, okay, if it works for them, then it's going to work for me.

50:39Turner Novak:Yeah, I feel like social proof is very, it's like underrated, but also like fairly rate. Like I think a lot of people like you kind of realize how important it is just to like have a couple other people tell you just like get you across the finish line, really with like anything, whether it's like buying product, even like listening to a podcast. It's like you see three people say like, oh, that has to with Austin Turner talking about how it was so good you got to listen someone will be like all right fine i don't listen to podcasts but i'll give this one a try yeah totally i mean i think the reason that you don't see a lot of social proof in in many launches is is not that they like don't think it's useful it's that it's that it's really hard to like have customers that are that like love your product so much that they're out there amplifying and that's like what made us so thrilled about the launch was that the amplification more than our investors it was our customers who like came out and were in the comments like the LinkedIn especially the comments in the LinkedIn posts that we had are just it's like just comment after comment of people talking about how much they love the product and and so that was just like super exciting to us that it felt like there was real substance to the launch of of like we are actually making these customers very happy we're making people's lives easier because they don't have to deal with something they had to deal with before and and they are like proudly shouting from the rooftops about that so we were really thrilled about that part and so when you when you do a launch like that like i remember i maybe i'm in like a a special group chat with you where you're like you're showing us the like i remember actually i think i was at disney world throughout the when you're talking about filming like how fast it went like i think you sent me a draft and like watched it like two days later but it was like finished or something like that because i was at disney world i was like a little bit disconnected and then like do you so when you're launching a product like that like do you involve the customers are like, hey, we just launched, tell us what you think of it?

52:27Turner Novak:Or do you just put out there in the ether and see what happens? Is there a good way to guide those and make sure they go a little bit better? There was some, so well, customers who had testimonials, obviously, I was sending those to say, hey, we'd love to do a testimonial with you. Can you give us some content for it? Or are you interested? Whatever. And so those folks definitely got a peek at some of the stuff. And then some other customers who are founders that I think are great at marketing. I was just sending them the work in progress website. The video, very few people saw the video. You saw it on the group text and a handful of other people, but not many people saw the video, partly because we were pretty locked in on the direction.

53:10So when we were riffing on the script and the concept, I was sending it to a bunch of different friends and getting their thoughts and but then like once we were kind of locked in on it it was like the types of feedback you don't want someone to be like well what if she says this instead of that and it's like oh we already shot it so we can we're just like read the editing phase like do you have feedback on the color correction or something so so like that was I mean we did send it to a few people though like one of the early cuts was like a little bit long and we got that feedback from some people and so we kind of cut it and so there was some there but But the brand and the web page was definitely like a ton.

53:51And like Sophia Amoroso, she provided a ton of feedback as we were building this brand. And so just like an ongoing kind of text thread where I was sending her some of the early web designs and things. And because with the brand, we also kind of went in a pretty like novel direction, which is that it's very people first. So we did a photo shoot with actual models that are like kind of laced across the entire homepage. And we felt like everybody in SaaS and productivity just has these like dark mode, purple gradient homepages that are all they're doing is showing you like screenshots or like kind of illustrations of features.

54:29And it's just like all just like features. And we felt like the experience we hear from customers is that they love Howie because it is like it engages like a human. They like that there are humans in the loop because they can trust it more because there's humans. and they like that it is solving, it is helping them with connecting with humans and whether it's like customers or investors and there's just like so much kind of humanness to all of it. And we felt like, why don't we then make the brand feel human? And so like some of the folks that we sent the early brand idea to, they were like, this looks like a makeup brand or something.

55:06It kind of does, yeah. Yeah, it totally does. But we're like, yeah, that's fine. Like we think our customers are awesome and we want to showcase like what we, the vibe that we feel like our customers have, which is just these great people who are real people and who are awesome. And we felt like photography was a much better way of doing that than like some illustrated figures or characters or whatever, or just like screenshots of like how you're writing an email.

55:38Turner Novak:and yeah like if if you did show screenshots the product it's like oh cool a screenshot is super human a screenshot of gmail like it's like the meeting has been scheduled it's like it's a little bit harder to show much i guess the original version of the website though i do remember you had like a calendar like lots of blocks and you like kind of played around with like animations like as you scrolled of like how like it was kind of like scheduling but again it's like you know i feel like the to your point it's like a makeup brand like it does feel a little sexier in a way. Yeah, it just feels elevated.

56:09And that's like the thing is that people feel like a baller when they use Howie because it's like they used to have to do this thing themselves and someone's doing it for them now. And so it's accessible. It's not like it's like a high-end luxury good that nobody that is inaccessible, but it's also kind of baller. And actually one of the analogies that I used with New Kid, the agency early on, was Uber, like early days uber because it was like at the time you had yellow taxis which were like dirty they probably wouldn't show up if you called them but they might and they and like they're just like all these things that are that are like not great about that experience and then there was like the a chauffeur a private chauffeur which was like this baller experience that almost nobody has but the people who do just it's amazing and then uber came in as like they they positioned the brand pretty really like kind of luxury and high-end but it was also accessible and it was called the everyone's private driver and was there like slogan early on and and so it was like taking this luxury out of reach thing making it accessible but still kind of baller and that was like the one of the analogies that i had early on of like what i wanted howie to kind of stand for is like the executive assistant in this luxury thing that's that's inaccessible for most of us um but we all know it's pretty baller and then the alternative is calmsley which which which is a meme, basically, how inefficient and it is the taxi.

57:32And we are pulling that baller experience forward in a way where it's accessible to everybody. And that doesn't mean we need to cheapen it and make it feel more like a taxi. It can still be baller and elite and have really polished branding and feel really kind of... It's luxury, but it's also accessible. Yeah.

57:57Turner Novak:Two things that the way you said reminds me of is like when you get introduced to someone and there's like, you know, they add their EA. Some people, you know, you might be like annoyed, like, oh, this person doesn't have time for me or whatever. With Howie, like that jumps on pretty quickly and it's like responds fast, but also like there's almost like the power element of like, let me add my EA. Like I'm so like there's almost this like you made it in life if you have an EA or like a secretary. So it's like you're like, I kind of hate the word democratize, but you're like democratizing and just allowing more people to have an EA.

58:31Turner Novak:It's kind of like in between of like sending someone a link and then actually having like a human assistant that, you know, you're paying, you know, possibly six figures all in of comp, of taxes, or security, health insurance, salary, etc. and it's interesting I remember when I first met you when it was investing I was like I don't know man Calendly like a better Calendly like is this is this really an opportunity but I think in 2023 Calendly did like 270 million in ARR or something like that it's probably a lot higher now and this is almost like a little bit of a more fully baked version so like the opportunity is actually a lot bigger maybe than someone would think just from initial, initial glance.

59:14Yeah. I mean, to me, it's like even just that, like, Calendly is a great business and it's awesome. And it solves one thing really well, which is like find a time for a meeting. But when you talk to executive assistants about the calendar tasks that they do, find a time for a meeting is like one of a litany of other things. And so the scale of a business that just solves the calendar entirely for millions of professionals, I think, can be at least an order of magnitude bigger than Calendly. And then it's like, have we built the framework and the brand and the trust and all these things that allow us to go from just like we are just a scheduling assistant to an assistant that does many, many things for professionals.

1:00:01and we aren't in a hurry to go from one thing to the next because, again, it's like nailing any problem that we purport to solve, we want to truly solve to a fantastic degree. And so we're not in a rush to layer on features for the sake of features, but over time, there's no reason for us to be constrained to scheduling and calendar over the long term. Yeah, well, to the point of time,

1:00:27Turner Novak:it's like time is money, right? Like that's the ramp slogan. time is money, save both I love that there's probably some play on words with Howie like time is money

1:00:39Turner Novak:you could say save both with Howie I don't know you can't steal the slogan exactly that's like one of my favorite lines of copywriting I've encountered in many years it's like time is money is colloquialism so they're not breaking new ground there and just save both adding two words It's just so beautifully simple and resonant. And many marketing slogans over many decades have tried to sell, save time or save money or save both of them. And it's amazing that they found a tagline with that that just in hindsight feels like it was just sitting there to be grabbed by anybody. Yeah. So you kind of mentioned there's probably opportunities to expand over time.

1:01:26What does this look like?

1:01:28Turner Novak:Like what is how we look like over the long term? Like I'm talking 10 years, 20 years in the future. I don't know. I don't know how far out you think about this stuff, but what do you think the big kind of opportunity is and what the product might look like? We try to focus most of our energy on what is right in front of us. And so it's like, we think a lot about like, if we achieve what is right in front of us, which doors does that open and where might those lead? But we try not to obsess too much because I think it's really common in startups to be way too focused on like what your company is going to look like when it's doing a hundred billion dollars in revenue and you haven't actually built something that people want to use for ten dollars and and so we do really try to focus on like what is right in front of us and how can we better serve the customers we have and and have end the day with more customers than we started with every day and like that that's really like where most of our energy is but we do think about like where does this go and i think there are different paths like you could see it being a kind of single player use case where it's like all of our customers are individuals using Howie and it spans industries and like consumer use cases and professional use cases, but it's just this like super assistant for the individual.

1:02:41Or you could see it being this like calendaring scheduling product that's sold into 10 ,000 person organizations where it's like the assistant is a part of it. And then there's also all this architecture around like helping a company know where time is being spent and which meetings are happening and which aren't happening and how many people are in the different meetings and lots of different things around just like making, creating efficiency in a large team with the calendar. I don't know really at this point. Like I really think the technology we're building can work really well in both of those paths.

1:03:11And there probably are 10 other paths that I haven't thought about. I think we're excited about both. We definitely are excited about like the, even without having built many team features, we're still seeing a lot of adoption among teams. Like Ramp, since we were just talking about them, Ramp's recruiting team uses Howie And that has been really awesome because that's one of our first larger teams that's using it. But we're seeing organizations where we grow from one person to three people to seven people to 10 people. And we haven't built much functionality that kind of incentivizes that, but we are starting to.

1:03:45And so over time, I think the main thing that is like a clear North Star is we think that professionals of all sorts spend a ton of time on meta work, which is just like work about work. So it could be scheduling. It could be like setting reminders to follow up on something. It could be like reviewing notes from your calls or anything like that. there's just like any ton of things that all of us spend time on that is meta work. And, and there's also a lot of meta work that like lives in our brain at all times. So we're constantly thinking like, I have to follow up on that, with that prospect. And do I have enough time after this call to get to the next, to get to my like coffee meeting this afternoon?

1:04:29And do I like, I don't know, did I, I got that customer support email over the weekend. And I think I was like, totally dropped the ball in responding to that. And there's like all these things that just live in our head and if how we can just be plucking those things out of people's brains so that they can have the confidence that the thing's not going to get forgotten and is going to get taken care of, then that's great. And so we're more interested in solving the meta work than like building an assistant that does the actual, like your actual job for you, if that makes sense. And anything that you could classify as meta work is probably something that we are intending to solve for professionals over time.

1:05:07Okay.

1:05:07Turner Novak:Yeah, that's something to look forward to, I guess. There's a lot you can do. As a customer, there's a lot of things that Howie could probably do for you. Yes, totally. And it'll start with just breaking out of email. So we're building Howie for SMS right now, which I'm really excited about. And it will be just a much quicker way for people to interact with the product. And we eventually will have Microsoft Outlook support, hopefully by the end of this year. But we'll see. We've kind of like... There's enough demand in the Google ecosystem that we haven't been in a huge rush, but we also get emails like literally 10 times a day asking us for Microsoft Outlook support.

1:05:46So it will unlock a lot of potential new customers. And so that's really valuable.

1:05:50Turner Novak:But I mean, Outlook is enterprise. Like when you get Outlook, you're going to start signing those like thousand seat, 10 ,000 seat deals. So that might be valuable. Yeah, totally. I mean, there's tons of market opportunity there. We don't really have like a good offering for 10 ,000 people to use Howie today. But as we go, like, yeah, I mean, we get interest from any number of like company size, industry, like people are reaching out. And we just have had to kind of like keep the blinders on of like, we serve people who need to book a lot of external meetings and have a lot of pain in doing that.

1:06:26And that's like just limiting because we want to serve many, many more people than that over time. But it's allowed us to have like a ton of focus on just better serving those people and understanding that kind of need and just nailing it. So that's where we are now. But yeah, but we'll add Microsoft for sure soon. Yeah. And actually, I meant to ask this earlier, but I mean, you mentioned we're growing 30%, 40 % a month.

1:06:52Turner Novak:Like what's the current state of the business? Is there like a public or even like a private, like you're only saying it on this podcast, What's currently the size of things, the state of everything? We went into the launch with over 1 ,000 paying customers, and we have grown our customer base a lot since that launch. So that's really exciting. And what else can I talk about? Oh, how he's booking well over 5 ,000 meetings a week for our customers. So that's a pretty exciting metric. And he's interacting with tens of thousands of people every month on email. You see it. The investor updates. We just have been growing.

1:07:29Turner Novak:Yeah, that's fair. Well, I mean, I don't want to be the one to say, I want you to be able to say. I know. Yeah, I think those are the main like kind of public numbers right now. Okay, so actually going back to like the early days, you kind of like you talked about 2015, the Slack bot or like the Slack channel, you kind of skipped ahead like, you know, eight, nine years later, but there's a period in the middle. I think one of the most interesting things you did was you worked for Jason Kalkanis. And you said, people are always curious. what was that like and i am also curious what was that like working for jason yeah everyone everyone always wants to know i very regularly meet people who immediately when they learn that i worked for jason they want to know he's good at what he does obviously like it's not like an accident oh yeah so he's a really close friend i was gonna be like he's a fucking moron no um And so Jason and I definitely would have pretty intense arguments and things.

1:08:29And I think what I really respect about Jason is that there are a lot of people... Our entire industry lives on Twitter. And so I meet a lot of people who I've gotten to know their Twitter personality over time. And then I meet them in person. And it's pretty common to feel like a disconnect then where you realize there was this fully kind of manicured persona that somebody created around themselves. And what I respect about Jason is that he literally lays himself out there and he is actually like the person that you see online. And so you might love him, you might hate him, but I respect the kind of ability to actually be yourself online because there's a lot of the algorithms and the kind of social norms and all these things pull us to try to present a manicured version of ourselves.

1:09:20And so it's actually pretty hard to just genuinely be yourself out there. And especially if being yourself is a polarizing person that's going to piss a bunch of people off. And so I really respect that. And I definitely learned a ton from Jason about investing and a lot about him. So back then, this was like 2016, he was studying constantly. Like he would be, he would, I would get in his car and he, and he would like sit there and make me watch like 30 minutes of Charlie Rose interviewing someone or Oprah interviewing someone or Howard Stern interviewing someone. And he was like literally like studying the tapes of these interviews.

1:10:02He'd watch the same interviews over and over and over again. And at the time I was like, do you really learn anything from this? And now I can see, like once the All In podcast came out and he had to like serve as this pretty challenging role as moderator for a bunch of really powerful personalities that all want to hear themselves talking and including himself also. And so I can see that that work that he was putting in for years and years and years and studying the art of moderating conversations and interviewing people is actually working. And it helps that he doesn't mind being the kind of punching bag in a lot of the conversations.

1:10:45So that's all cool. And yeah, I mean, it was interesting. He definitely, as you would expect if you followed him online, can be brash. And so we definitely had some pretty heated arguments where we disagree about things because both of us are pretty passionate people. And so there's some funny experiences, there are memories there. But overall, I think that it was fun to work for him. And he's been the first investor in two of my companies now. And so the, like, he's definitely a person who has deep loyalty and, and I've felt that. And, and, and so like, it's cool that from the day, first day that I ever met him, I have felt like he truly like has my back.

1:11:30And, and, and so like, as much as he could be a dick or he's polarizing, there's all sorts of things on mine that I, that I like may or may not agree with, or that I'm just like, why are you saying this? and so there's all of those things but at the end of the day it's like that it's you don't often find somebody who who you feel like actual real loyalty from and to and and so yeah so he he's a good

1:11:57Turner Novak:friend and he did i mean did you learn a lot about media from him because he really runs like pretty interesting pretty like a media company yeah totally it really is more of a media company than anything and i yeah a ton and like he and he's been doing it forever i mean he was like like talking print magazines in new york and silicon alley something i can't remember what it was like 90s right like yeah he's been like doing this forever and he he knows everybody and he's seen so much and so that is like one of the things is that i started to learn is i would often think he didn't know what he was talking about and then and sometimes realize that i was right but more times realize like oh actually he's like really done this shit and he knows and he knows what he's doing and yeah so like the with media specifically like i really think he has a good grasp on how to do it and and i mean even just he was investing in video content for his podcast at a time when nobody else everyone was just doing audio only and like he would have cameras for every do every single podcast interview in person never remote and never audio only and and that was just like ahead of the curve and now he has a back catalog going back 16 years or something of these video podcasts.

1:13:11And, and so yeah, all sorts of things like that, where it felt like he had a pretty good grasp of like, what, where, where the media world was going and what was kind of resonating. And then also had a willingness to just kind of keep going forward because like, there's, you see a lot of people kind of try to start a podcast or start some sort of form of media. And then just like, when it doesn't become the next big thing in three weeks, then they just kind of like fizzle out and abandon it. And there's a lot of value in just like continuing to do the next episode and the next episode, two episodes a week, you just keep going.

1:13:45And, and that over time, like really does compound. And so the determination is definitely a big one too.

1:13:53Turner Novak:Yeah, it's hard. I mean, I've been doing my podcast for like two and a half years at this point. It's almost like unpredictable. Like I'll be like, oh, this one's gonna do so good and then I'll post it and it's like the worst one of the year or it'll be like one like I mean honestly when I go back and look at the data like I did I could not have predicted what the better episodes would have been it's like with all content like even with Twitter like some of my most viral tweets they got like 10 million views there's like a typo because I like posted on my phone really quick and it did like auto correct I didn't realize it and then there's some where like you know you spend like an hour on and it gets it gets like one percent of you know whatever what you thought it was going to get so it's like a lot of it's just like a volume like it's just shots on goal like it's just staying in the game keep putting stuff out there i think that's just generally the thing with like really like media or like the internet or content on the distribution side is like a lot of these algorithms the way they work like you can there's like almost like unbounded upside like right like there's like a hundred million people that might potentially see the content and it's just like figuring out like how do you get in front of all those people but you never know what's going to work and so if you're only posting once so you post once a month right versus if you post once a week once a day once an hour just like the more you're putting things the more shots on goal you have the more surface area like chances that you'll people see your stuff i guess you got to balance like not being annoying also yeah i mean that is tough it.

1:15:25Turner Novak:Yeah. So just post about what you're doing, tweet about what you're doing, put content out there. That's like natural to you. That's easy. That like kind of fits in with like what you're good at and like what your unique advantage is. And I don't know, I feel like not enough people think about it that way. Yeah, totally. And it's, I mean, it applies to like anything, building a product and building a business. It's like the, you can get so distracted in where you want to be or in like how difficult the challenges in front of you are. And for us, like every day of building this company has been just like, can we get one rung higher on this ladder?

1:15:58I mean, we chose a problem that's like definable of like scheduling. And so it's like, can we be, early on, it was the only thing was like, can we be better at scheduling today than we were yesterday? Now we have a business, we have customers and all these other things. But, and so it's still, it's like the same thing I said before, how can we end today with more customers than yesterday and end today with better solving the problems that our current customers have today than yesterday. And it's like just doing that, then the compounding kind of starts to happen. And so it can really apply to anything, I think, that the idea of just like, you just need to move forward a little bit every day.

1:16:36Turner Novak:Yeah, so speaking about compounding, I know you've had just like pretty steady, continuing to grow product kind of, it's interesting when you, it's like you think about how someone maybe discovers Howie, it's probably in their email inbox. Like that's maybe the place they discover it. do you remember how did you like first get people to start using it was it just you know a lot of people and you're like hey i'm building this thing check it out kind of took off from there what was kind of the process yeah the first so we like put up a wait list early on and people started to sign up and like i had it in my twitter bio and there were a few people early on who started using it and then like tweeted about it and and that would lead to like because at the time the product was not very good but it was good as if you like there was at least like a 50 chance that your first three interactions would be fantastic and so then that people would lead to people tweeting about it and then and then eventually they would like run into the issues and and so but it would like so that was enough to validate the demand and then the waitlist kind kind of started to grow.

1:17:42And so then we would like kind of look at who's on the wait list and, and go reach out to people. And we have a couple of the very first customers we ever onboarded are still using the product today, which is remarkable because they really like rode through the, I mean, some of them who are friends that like that, that's still remarkable. Like Alex Cohen, for example, used it all the way through and was not like dissatisfied with the old product. But then once we rebuilt, it was just like, this is mind-blowingly better. and like I can use it for everything now. But there's some folks that I don't even know who were in the early cohorts who have continued using it.

1:18:18And, but yeah, the word of mouth definitely is a huge aspect of it. So it's like people see Howie in the inbox. We don't make Howie's emails an ad for Howie. We try to be really subtle in that regard. So it's not like there's a link to the website or anything in those emails. And so it is really subtle, but then also just people that are having a great experience. The reason the word of mouth growth really kicked in in January of this year is that the product experience became something that people just really want to talk about. And so that's a huge part of it. And then, yeah, there's been some viral moments and things along the way.

1:18:51But again, it's just this steady process of we went into September with a thousand customers and we want to end September with more customers than that. And now we're in October with the number of customers that we have and we want to end this month with even more. And so it's like, we can try to manufacture viral moments, or we could do like a marketing campaign or whatever else we want to do. But ultimately, it's just, it's like, not trying to catch lightning in a bottle. It's just like, how can we reach a few more people today?

1:19:22Turner Novak:But you were telling me the other day about you had this really interesting strategy of doing your pitch deck that kind of unique, kind of like simplifies the process, but you think it works pretty well. What's your strategy for making a deck? Yeah, so I've looked at a lot of like Docsend metrics. Docsend, when people send a pitch deck, I suggest sending a pitch deck via PDF, not via Docsend link. But I've looked at a lot of Docsend metrics and gotten to glean a really interesting fact that I haven't heard a lot of people talk about, which is that the vast majority of people you send your pitch deck to are going to click through all the way to the end.

1:19:57They're going to make it to the end. But the vast majority of people who you send your pitch deck to are never going to spend more than three seconds on a single slide. So if you have 100 slides or if you have 10 slides, they're going to go three seconds per slide all the way through to the end. And so what you can do with that information is not optimize for how do I get less slides, but optimize for how do I get less information on a given slide? Because you know you get three seconds, whether it's your 20th slide in the deck or your third slide in the deck, you're going to get three seconds of someone's attention.

1:20:29And so more slides with less information is by far the best thing to do. And so basically the strategy that I have is write it like a thread of tweets. So you create bullet points. You should have not even 140 characters of words per slide, like eight words per slide or something. And the shortest possible thing, have a narrative arc that pulls people through. So I don't love the kind of like standard templates of problem, solution, whatever. Like you need to get, you need to hit all of those things, but you should have a story that gets somebody like to, to want to go to the next one. And then, and then again, put an amount of information that can actually be digested in three seconds.

1:21:08Cause even your friends that you send it to for feedback are going to scroll through three seconds per slide. And someone who's serious is going to later maybe go spend more time and look at like, and really like read through each slide slowly. But, but to even get the chance for the slow one, you have to have passed the three second test. And so don't worry about like some, I've seen some people recommend like, make sure you have less than 10 slides because you don't have much of someone's time. And they're correct that you don't have much of their time, but they're incorrect that you should jam like a ton of content into 10 slides.

1:21:39You should just stretch it out farther because they're going to give you three seconds for every slide and then they're going to keep paging through. And so that's my advice is create a slide deck that has very, very, very short bits of content, has some narrative arc that pulls me through to the next slide. and get all the points that you want across, but never try to make more than one single nugget of information fit onto a single slide.

1:22:06Turner Novak:So it's interesting to me. I was like, I need a problem slide, I need a solution slide, I need a market slide. The problem slide might be five slides, and it's just one sentence with a graphic or whatever for each almost phase or setup of the problem to get you to, by the fifth side, it's like, holy shit i get the problem yeah 100 the next set is like yeah it might be like a couple couple screenshots of the the way you solve the problem or like sentences and how you solve the problem and like however you need to find the market opportunity like maybe it's a couple slides and again it's like just really because to your point people don't read like a lot of the times people be like there'll be like tons of tax everywhere and you just read like the header or like what's the most bolded image or like thing that stands out?

1:22:52Nobody is reading a paragraph of text on the deck that you sent. And people spend a lot of time on those paragraphs and every word of them, and then nobody reads it. So instead, figure out what you can do in three words and in four words and get that whole paragraph, but just stretch it across more slides and punchy short sentences that actually tell a story and then people will actually read it. And otherwise, like, they're just going to keep moving. So even three seconds might be generous. You're not going to spend a lot of time per slide. So you want to get the least amount of information possible.

1:23:25And then obviously you want to only include the most important information and you want it to feel like a teaser. You want someone to leave afterwards wanting more. And so you got to kind of cut it before they're fully satisfied. And you want them to have questions because then they have to take the call to answer the questions. There's a lot of things beyond that, but it's like, just never try to fit more than 0.2 ideas per slide or something like that. Yeah, that makes sense.

1:23:50Turner Novak:It's a good strategy to think about. And you've kind of mentioned before in the past when just we were talking that people tend to optimize for growth too soon. I mean, I guess there's different things you can mean by that, but I guess why do you think that's the case? Because don't you want growth? You want PRR to go up super fast and like you get a higher valuation, raise money, right? Like, isn't that good? Yeah. So I do think it's good, but I think if what you're trying to build is durable value, there are many proven ways to kind of growth hack a product and to optimize your push notifications to get people back to it and to do all the things that make the metrics look the way that you want them to look.

1:24:35And I've done all those things in the past. And I've experienced building a product that has all the growth levers kind of optimized and tuned and it's still not growing. And that really sucks. Because then it's like, okay, we tried all the things and still nobody cares. With this product, I don't know if it's the nature of it being in the inbox. I think that's part of it. And then maybe the clarity that we've had since day one about the problem we're solving to where we never had time to work on growth hacks. Because instead, we just have had to work on fixing the problems with the product. And that continues to be the case today.

1:25:12And so we've never had time to build out. We literally don't even send emails. You sign up as a new customer. We don't send you emails to remind you to use the product or teach you how to use it. You get one email when you first signed up. and we're going to add drip campaigns that go out and we're going to add more user education, like here's how VCs use Howie, here's how founders use Howie and all that type of documentation and stuff, which admittedly, it's not ideal that we don't have those things. But the thing that is ideal as a result of that is we've just lived in the ground truth of is this product useful?

1:25:48So you sign up for Howie, you don't ever need to come back to our website again. So you use the product by going into your email client and remembering to type in Howie's email address. And we don't send you a push notification to encourage you to do that. We don't like there's no bookmark that you save in your browser. There's, you know, you don't get how he doesn't just like email you. Actually, now he does do email you proactively for like conflicts and things. So we've, I guess, add some of that proactive stuff. But that even six months ago didn't exist. And so there is like, I guess, some proactive things, but for a while there was none.

1:26:22And so the retention, the word of mouth growth, the usage numbers and all those things looking so great was really kind of validating for us because we're like, we are in the ground truth. There's no, we're not tricking people into coming back and we haven't optimized, we're not pulling any of the leverages that we could pull over time. So over time, you want to, for sure. But if you genuinely want to be intellectually honest with yourself about, is my product valuable to customers, then peeling away all of the growth hacks is a good way to actually do that if you're willing to. But it's hard because it's like you want the numbers to go up as fast as possible and you want it to look like you've solved the problem, not that you are solving the problem.

1:27:04But we have treated it as an intellectual experiment from day one of can we make this product useful to people? And that for us really, really helped us get to a product that people actually want to use because there was no smoke and mirrors in the metrics.

1:27:21Turner Novak:so it's almost like just don't even focus on growth at all and if the product is growing that's probably a good sign yeah you know that's products in the world grow themselves yeah so it's like why why should you have to like spend a bunch of time on like the sharing functionality or the referrals or why should like why should you even have a referral program for a product that's like in the early stages pre-product market fit and why why should you spend any time on that if the product is not so good that it's growing that it's growing by word of mouth and so if you can just every day try to get closer to a product that people can't stop talking about then your time is much better spent i think yeah and i guess too the way that the product works it's like a it's sort of like a multiplayer product because in order to use it there's somebody else there that sees it so that probably helps a little bit on the growth side is just generally speaking i'm sure you get people to sign up is like oh what's this howie thing like howie.ai or howie.com i don't know what you are or someone might obviously use the custom url so maybe maybe you don't even see it yeah yeah one i mean like sometimes people don't know one that i saw the other day that was hilarious is a white label howie so the person thought it was a human and then but the person went through the whole scheduling experience and i think they had had to reschedule the meetings there's like some tricky element of it and and the person was really impressed and they sent an email to the Howie customer and to the white little Howie saying, do you have any friends?

1:28:49Like, I really need someone like this to do my scheduling. So they like thought it was a human and were trying to like hire the friend. And then, so then the customer was able to just be like, oh, just go to Howie.com. It's 35 bucks a month. And you can have like literally the same assistant. You don't need one of his friends. And - No way. Yeah. So like that, it does happen for sure. Sometimes through like direct word of mouth or everyone's just kind of always talking lately about like what AI tools are you using. And so if people like, I hear these stories of like, I was at this coffee meeting and my friend asked me what AI tools I'm using.

1:29:21And I said, Howie. And they said, wait, like the thing you use to schedule this coffee meeting. And I said, yeah. And so like, it happens that way. We're less than like, again, we don't put like a link to Howie in the emails that Howie sends. And so there's a lot of ways we could be more aggressive in doing that, but we care about the product experience over everything. And so we just don't want to, dilute the product experience for the sake of a growth hack.

1:29:45Turner Novak:Yeah, that's always good. And when I first met you, you were living in Bend, Oregon. I think you're in Seattle now. What's the significance of living there? Like, shouldn't you be in San Francisco? Are you building an AI company? Yeah, so I had not spent a ton of time in Seattle before we started the company. Dave was living here and had moved here in COVID. Both of us lived in SF for like 10 years. And it does definitely help that we have like deep networks down there. And we didn't know at the start for sure what we were going to do, like build the team remote. Like we lived in different states at the time.

1:30:23So the two of us were remote. But over time, we started to feel like it made sense to set up an office in Seattle. And so we did that. And we started to kind of grow the team exclusively in Seattle. I was traveling here every other week. And so then eventually it made sense for me and the family to move here, which we did this summer. The reason that I think Seattle is awesome for us is SF is amazing, obviously. And there's a more vibrant startup community in SF than anywhere else in the world. And you just can't compete with that. And there's more tech talent, especially tech talent that's interested in startups.

1:30:55There's more in SF than anywhere else. But the challenge that friends of mine are having is there are the coolest companies in the world are all in SF. So every three months, YC has a new batch of 200 companies that all raise$3 to$5 million. And they're all competing to hire engineers within a seven square mile block of California. And there's only so many engineers for those people to hire. And three months later, there's another batch of 200 companies. And then in addition to that, there are all the coolest AI startups that you can imagine from seed stage to series A to series B to series C to series D to public companies and everything in between.

1:31:34And so the competition for great talent is just insane in SF. So friends that I have who are in SF and are excited to build their team there and be fully in the office have then ended up building a remote team because they literally can't find anybody. And so Seattle is interesting because there's a ton of talent. There's a lot of AI talent because AI has been happening here at Microsoft and Amazon for a long time before it was kind of cool. And because of those companies also, there's a ton of tech talent. There's less engineers that are excited about startups. There's a lot like we got an applicant from an engineer a few weeks ago who is at Microsoft and has been at Microsoft for 31 years.

1:32:17and we were like, okay, you're not going to be a great fit for our culture here if you were at Microsoft for 31 years.

1:32:23Turner Novak:Who knows? They might be. Hey, they'll stick around for 31 years at Howie. That could be good. That's true. That's loyalty. Yeah. Yeah. So I don't know. But anyway, I think that there just aren't nearly as many cool AI startups. And so we were able to kind of stand out in that regard. And there's still plenty of tech talent. And then like most of our investors are down in SF, but we travel down there and know lots of those folks already. And so for us, it's like it's working really well and it's fun to be kind of building in a place where we feel like we can really like be kind of on the map, especially as we grow.

1:33:07Yeah, makes sense. One other question I wanted to ask you, but I know you do.

1:33:12Turner Novak:I don't think this is like your full time thing, but you do some angel investing. You actually work with your brother. You guys have a small fund, kind of like an angel fund. What's your pretty interesting, pretty good rap sheet? What's kind of like the greatest hits on the Austin and Stu angel portfolio? A long time ago, in 2014 maybe, we said we wanted to do investing together. And we found there's some Hacker News thread somewhere I can find the actual post. But there was a thread on Hacker News about angel investing. And Sam Altman wrote this comment that was like, here's how I did it. I made a couple of small angel investments with my own money because I didn't have much money to actually do it.

1:33:55But because those investments were good, I had track records. And so then people wanted to give me their money to invest. And then that allowed me to do a lot more investing. And then he rattled off that he was early in Stripe and Airbnb and all these things. And we were like, well, that makes sense because we don't have a ton of money to invest, but we want to do it. And so that seems like a logical path. And so we kind of decided, let's move really slowly and make investments that we have very high conviction in and build some track records so that eventually we can invest other people's money.

1:34:25And so first one we ever did, my brother Stu was working at Teespring and Jack Altman was his boss. And Jack one day said that he was leaving to start a company. We both had kind of gotten to know Jack. Stu got to know him really, really well, obviously working together. And we were like, he is phenomenally talented and motivated. And it was the earliest kind of stage. We were investing on a safe before they went into YC and they didn't have a name yet. They weren't totally clear on what they were building. And it was a$4 million post-money valuation. But we knew that we wanted to bet on Jack.

1:35:02We knew some of the co-investors who were pretty impressive names. And so we made that bet, which is Lattice. And now is doing like, I'm not even sure how much, but well over a hundred million in ARR. And so that's been an amazing story. And then the next investment, I was the first ever paying customer of Superhuman. And I absolutely loved the product and couldn't believe how fast the team was moving and how good the product was. I started using it when it barely worked. And then it kind of was progressing from there. And that was incredible. So I was just like, hey, Rahul, can we please put money in?

1:35:37So we did that one. Then a couple of years later, Mercury, I started my company, Capiche. And I had really frustrating experiences with SVB when I was working with Jason and we were using SVB. And so I started searching around online for like, are there modern alternatives to these banks? And found a post from Ahmad who said, like, I'm building an alternative. And I emailed him and said, hey, can I use it? And he was like, well, you'll be our third ever customer. And we're still kind of building the thing. But yes, you can if you want. And so I signed up and I was Mercury's third customer. And I got to like see, I have these email threads that from, it must have been 2019, where I was like reporting a bug to him because I was trying to get a wire.

1:36:25I can't remember what it was, but something. And it's like 10 p.m. on a Saturday. And then like 20 minutes later, Ahmad's like, I just pushed a fix. It should work now. And like, so again, like seeing the velocity and how much he cared. And obviously it's a huge opportunity. So then someone at CRV reached out to me to do like a customer diligence call when they were raising their round. And so then I emailed them out and was like, I just did customer diligence for you. I told them they didn't say not to invest. And now I know you're raising. Can I please put money in? And so we did. And yeah, and then we raised the first cough drop.

1:37:00We call it cough drop capital. My last name is now Peter Smith, but originally it was Smith because we merged. My wife and I merged Peterson and Smith to make Peter Smith. So Stu and I were the Smith brothers and there's like 150 year old cough drop company called Smith brothers cough drops. And, and so the name cough drop capital is a, from the homage to that we are, our dad and his brother had a boat called the cough drop when we were growing up. So that's where Cough Drop Capital comes from. And so, yeah, we said we raised the first fund, which is about a million dollars and still has a ton of active companies that are doing great.

1:37:36And then the next fund is$3 million and is like kind of currently being deployed today.

1:37:44Turner Novak:Nice. It's pretty small checks, right? Like 25K, 50K? Yeah, yeah, exactly. Nice. That's easy to slot into a cap table. yeah today I have like pretty much zero time for for investing and so it's mostly it's like sometimes customers of ours that are building cool things and I'm like hey can I put 25k into this thing or or like I don't know so it's it's like the the deal that fall in my lap that that are where I'm focused I'm not like going to YC demo day or like going out and doing taking pitch calls but with founders it's just like cool stuff that I'm using or or just excited about. Well, that's the thing.

1:38:20Turner Novak:That's like what everyone always says, why founders are good angel investors. They're just in the trenches. They, you know, people are asking for advice or using new products or trying things. People are trying their products. So like you just see different stuff than like some country club guy who, you know, is retired and maybe was like early Oracle executive or whatever. Like it's just, it's a totally different world. So yeah, yeah, totally. Well, cool. This is a lot of fun. Thanks for taking the time to do it. Yeah, thank you so much for having me. This was awesome. And thank you for listening.

1:38:52Turner Novak:Thanks again to Hanover Park for supporting this episode. Head to hanoverpark.com slash Turner for the AI native ERP for funds, integrating fund admin, portfolio management, and LP experience all in one platform. If you missed it, make sure to check out last week's episode with Chris Franz on building loops to fix email for developers. Tune in next week for Eric Barnhartson at Modo, building the AI infrastructure loved by developers. If you like this conversation, please like, comment, subscribe, name your next AI secretary after me, or just call it too much like I did. If you don't want to miss a future episode, subscribe to my newsletter, the split, T-H-E-P-L dot I-T.

1:39:32Turner Novak:Link in the description. And each episode of all the transcripts emailed directly to your inbox every week. Thanks again for listening. See you next time.

1:39:46you