🎧🍌 Howie: The AI Secretary | Austin Petersmith, Co-founder and CEO
Inside Silicon Valley's favorite AI assistant, why AI products should be very narrow, the makings of Howie's viral launch video, why you shouldn't grow fast, and a non-intuitive pitch deck strategy
Building AI assistants that work well is hard. So much so, that Austin Petersmith and his Co-founder Dave Newman built Howie into one of the most narrow AI products you can imagine: scheduling meetings.
We unpack why AI assistants are so hard to build, the decisions that led to Howie, and everything that went into building the product, brand, naming, and viral launch video, what it was like working for Jason Calacanis, and the unique pitch deck strategy Austin used to raise $6m.
Thanks to Hanover Park for supporting this episode and to Adam D’Augelli, Sophia Amoruso, and Alex Cohen for helping brainstorm topics for Austin.
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Timestamps to jump in:
3:35 Howie: The AI Secretary
6:08 Why AI assistants are so hard to build
16:19 Why Howie started in email
20:49 Adding a human in the loop
30:48 AI software vs AI-powered humans
36:21 How a meme inspired Howie
39:29 Inside the making of Howie’s launch video
44:15 Howie’s viral launch video + Discussion
53:47 Designing the brand
1:01:37 Long-term opportunity and roadmap
1:07:53 Working for Jason Calacanis
1:12:00 Jason’s media lessons
1:16:51 Getting Howie’s first users
1:19:35 Pitch deck strategy that raised $6m
1:24:09 The mistake of optimizing for growth too soon
1:29:48 Building an AI company outside of SF
1:33:13 Being Superhuman’s 1st customer, Mercury’s 3rd
Referenced:
Try Howie
Jobs at Howie
Howie Dewitt on Know Your Meme
Find Austin on X / Twitter and LinkedIn
Related Episodes
👉 Stream on YouTube, Spotify, and Apple
Transcript
Find transcripts of all prior episodes here.
Turner Novak:
Austin, welcome to the show.
Austin Petersmith:
Thank you so much for having me.
Turner Novak:
Yeah, I think this will be fun. We were talking right before we started recording, all the stuff we’re going to hit on. Really quick though, for people who are not familiar with Howie, can you just give us a quick high-level on what it is?
Austin Petersmith:
Yeah, so Howie is the modern secretary. He’s a mix of AI and then also we use humans in the loop to correct some mistakes before they happen and totally focused on scheduling. So, he’s email-based. You email Howie at howie.com or can even white label him and give him a different name and an email at your domain, and anything that you do with your calendar that is tedious, Howie can do it.
So you CC him on a thread and he can offer time slots, he can reschedule meetings, set up Zoom links. He knows where you like to take your in-person meetings, can pick up subtle signals, like maybe a secret phrase that means a meeting is low priority and then he’ll schedule it far out in the future and will notify you if there’s conflicts coming up on your calendar. If you have a meeting coming up that you haven’t RSVP’d to, to just help you with your general calendar hygiene. And he’ll click calendar links for you so you don’t have to click on those, and can look at other people’s calendars within your organization.
So if you’re scheduling a call externally and want to offer the overlap of your availability plus to other people, then he can do that. And so anything a great assistant can do involving the calendar, Howie can do.
Turner Novak:
Yeah, I think my favorite feature is the giving it a different name. So I had a tweet a couple of months ago, I called mine Chamath and that got, I don’t know ... I think you said it was one of the best days for the company for new revenue when I tweeted that. I called it Chamath and then ...
Austin Petersmith:
Yeah, it was right when we had rolled out that feature, and people want that feature because it’s super cool to be able to name it. So, most people have not done kind of ... Most people have done more serious names, but we’ve seen a huge mix of different things. Some people call it bot@whatever because they really want it to feel like AI and other people create a whole persona of an actual kind of human and name it based on that.
And so we’ve seen a really wide mix, but we have tons of them now and it’s really fun to see. And we’ve seen also, times where there’s two Howies on the same email thread, but it’s like Victoria and George, and they’re interacting with each other and they’re both actually Howie under the hood, but they’re these two different identities.
Turner Novak:
It’s like that meme with the interconnected brain going, the AI ... The AI is going back and forth.
Austin Petersmith:
Exactly.
Turner Novak:
And so you mentioned one thing that I want to talk about later, but you said there’s a human-in-the-loop element. I know that was a big decision on doing that. We can hit on that a little bit, but you kind of had to do that because it’s so hard to build this thing.
Why is it so hard to make an AI assistant that specifically lives in your email? It kind of seems like the easiest possible thing you could build, really with AI.
Austin Petersmith:
Yeah, so I mean, the email architecture is not the hard part, but what is hard is there’s a lot of context in email threads. By the time Howie gets CC’d on an email thread, there might be 10 messages that went back and forth already that involves lots of mentions of dates and times, people’s email signature is mentioned, times or time zones or locations. And the actual metadata in the emails has lots of times and dates in it, and the time zones often are different from one to the next. And so there’s a lot of red herrings in an email thread.
And then there’s also a lot of human intuition in deciding what to do. When do you actually respond versus not respond, and subtle signal that people include. And all of these things, you look at them, none of them are hard 100% of the time, but they are very hard for an AI model to get right 100% of the time.
So it’s like the models can easily, 50% ... Two days into building this product, we had 50% accuracy that was just like ... Half the time, it does exactly the thing you want and then it’s like this climb where each 1% past that is harder. And so the main thing that makes this really hard is that mistake tolerance is very low.
So if ChatGPT makes a mistake, then you just kind of move on. You’re like, “Oh, ChatGPT made a mistake.” GPT‑3.5 was a phenomenal product, the fastest growing product in the history of the world at the time, and it was pretty bad overall. It would make tons of mistakes and hallucinate and couldn’t get a lot of really basic stuff right. But scheduling, there’s a very low tolerance for mistakes.
We, one time sent a customer to a coffee shop and we had forgotten to include the other person on the calendar invite, so he was sitting at a coffee shop waiting for a meeting that was never going to happen because the other person hadn’t been invited. And you can’t make that type of mistake very many times.
And so when people, our customers schedule with their investors, with candidates they’re trying to hire, with their customers, those are just not interactions that you can afford to screw up. And so the low-tolerance for mistakes is a big part of what makes it really high. And so you’ve got to be able to create a lot of human intuition in the product where it understands what people are trying to say and it doesn’t get ahead of its skis in terms of trying to engage in the conversation too much versus just focusing on the scheduling aspect.
And then there’s just a lot of ways that mistakes can be made when you’re scheduling across time zones and scheduling with a whole bunch of different people who have all shared different things about their availability. And so there’s just a lot of ways that these things can fail on the margins.
Turner Novak:
And I know this is kind of a long time in the making, the product. Where did it first kind of start?
Austin Petersmith:
Okay, so my co-founder, Dave and I worked together a long time ago, 2013, 2014. And then in 2015, we Slack introduced the Slack platform functionality where you could build a Slack bot, and we built a Slack bot that was like, you put it in your company’s Slack and you ask for anything.
And we quickly got a bunch of people using it, who really liked it. So they would ask for whatever they wanted. They’d be like, “Review this stack of resumes for me,” or, “Schedule an offsite for my team to go to Cancún next month,” or something or, “Get sushi delivered to our office on the Lower East Side right now.” And whatever the tasks were, we would just figure out how to do them and-
Turner Novak:
Wait, wait. So was it AI or you’re literally doing this stuff on the back end?
Austin Petersmith:
Yeah, so it was totally humans, but our idea was that it would be humans, but we thought we can build a bunch of regex tech ... We can build some technology that will streamline the requests so that we can route them. And by the time that a human sees it, it’s kind of been through some filters that simplify the task and make it repeatable. And we thought we could build technology that would make it scalable.
We quickly saw with the variety from one request to the next that there was no technology to build. If we were going to build this business, we were literally building a call center, and we decided not to do it because we’re like, “This is crazy,” and that was 2015.
Then years later, we both were playing with LLMs a bunch. We’ve been closed ever since and have talked about building something together over the years. And so a year and a half ago or whatever we were like, “Hey, maybe actually now we could build that thing we tried to build, but have it be technology this time.”
And we started prototyping a little bit and quickly came to the conclusion it still is not possible to build the generalist assistant that you can ask to do anything. We did see at the time, a bunch of companies that had raised money on that promise and still now none of them have really caught on.
Even Microsoft Copilot is an example of that. It’s like it reports to do 1,000 different things, but it doesn’t do any of them particularly well. And so we felt like the answer here is pick one task, and a task that you can do really, really well and blow that out of the water. And then over time, layer in more and more.
And so we chose scheduling because we thought it’s a frequent, tedious use case for billions of professionals around the world. No matter what industry you’re in, scheduling is a time stock on you that happens every single day. And it has distribution kind of built in because there’s usually multiple people involved in a scheduling interaction.
So, a scheduling product that does well will get visibility to other people and can kind of grow through PLG in that way, and then it felt solvable. It’s narrow enough that we can actually solve it. And we were naive on that third point, which we’ll talk about, kind of some of the challenges. It has turned out to be a lot harder than we thought to solve it, but we’re proud that we have delivered a product that really stands out in the market on this narrow task. And so if we had picked anything less narrow than this, we would’ve really fallen on our faces.
And instead, what we picked was what we thought was not too difficult to solve, and instead it turned out to be difficult to solve, but it’s still a really great starting point where we’ve built the flywheel and the architecture and all these things to solve the one thing and then we can do more and more over time.
And so that’s kind of the origin story, and we really quickly validated that people want the product and are willing to pay for it. And more slowly, we were able to get to the product that we have today that actually works.
Turner Novak:
Yeah, because it’s interesting that it’s so narrow and niche or just specifically the one action of scheduling a call. I remember when I first met you, it couldn’t even do in-person meetings. To your point about messing it up, it was so simple, but also it was super broad.
Everyone takes meetings, so it’s narrow and niche, but also extremely broad at the same time. So it’s kind of like this interesting Goldilocks, just the perfect amount of finding where you enter this personal assistant AI agent entry point into expanding the use cases over time.
Austin Petersmith:
Yeah. I mean, I think for other people building AI agents, there’s a lesson there because there’s a tendency ... It’s scary to put a product out into the world and there’s a tendency to then, because it’s scary, you want to try to have it be able to do more. So it’s less likely that a person is like, “Oh, that’s not for me,” because there’s just more things that it claims to do.
And LLMs have made this even trickier because you can throw anything at an LLM and get something back. So if you’re making an AI agent it’s like, “Why not let it go research the web for our customers, or why not let it, I don’t know, do whatever other thing that’s just an API call to GPT?”
But the narrower you go, even though that’s scary, it actually allows customers to self-select. You don’t sign up for Howie if you don’t schedule lots of external meetings, but if you do, you’re going to have a phenomenal experience and you’re going to absolutely love it and it’s going to be indispensable for you.
And after they self-select, it also lets customers know once they start using it, what to do with it. And so there’s lots of generalist AI products out there that... I try all these tools and there’s lots of them where I’m like, “Okay, it said it can do all these different things. What do I even start with and which one is actually going to work for me?”
And with Howie, we don’t have that because it’s just like you use it to schedule your meetings and that’s what it does. And if you’re not interested in that, it’s probably not going to be useful to you. But if you are, it’s going to do a great job at that and you’re going to know how to use it right away. And we can stand behind the experience you’ll have within that because we’ve designed it very carefully, and so it’s going to work for you, and it’ll be become indispensable for you and you’ll build a lot of trust. And then when we start doing the next thing, you’ll already have that trust in place.
Turner Novak:
Yeah. Even when you talk about how hard some of these things are, even with ChatGPT, for a while I just didn’t know what to do with it. Sometimes with these products, you need someone to tell you. I think there’s a reason that tutorial videos are so important. Just how do you use insert X product? I’ve been using Attio, it’s like a modern CRM, and the product is pretty complex. And you just watch YouTube videos, “Oh, that’s how you do that thing,” or another one would be Notion.
I’m sure when you first started using Notion, you’re like, “What do I even do with this thing?” But you watch a video of, “Oh, you can use it to plan out a product roadmap or internal Wiki or content calendar.” I use it to plan a podcast, use it for pipeline and for investing, things that I’m looking at.
And it’s like, you kind of know maybe you could do those things, maybe, but just seeing it and having somebody explain to you how to do it, it does help. But again, it’s super simple, granular, people know exactly what you use it for. How did you decide email, because I think it’s probably one of the very few AI agents that I’ve seen that lives in your email? It’s kind of like a interesting entry point. And it was just a function of scheduling meetings, most of it’s done in email?
Austin Petersmith:
Yeah. So I mean, types of scheduling happen in a variety of different places. So a lot of internal scheduling mostly happens in Slack and Microsoft Teams. And I hear a lot from crypto people who are like, “I want to use your product, but I need it to support Telegram because that’s where I do all my scheduling,” or Signal or whatever the different apps are.
And then tons of customers from the beginning have been like, “I really want text messages because I do scheduling on texts, or I want to be able to text Howie to say, ‘Put this soccer schedule on my calendar,’ and it’s just not conducive to me to switch to email for that type of thing.” And so it’s just lower friction to fire off a text message.
But for the coordination of external meetings, email just is where that happens. So it’s where booking links are sent more than anywhere else and it’s where the back and forth of, “How about this day? How about that day?” or any of that. It just happens on email more than anywhere else. So it made a ton of sense as a place to start.
And then it also is a fun place to build an AI product specifically because when you build for text message or Slack or any of these other things, people expect it to respond at the speed of ChatGPT, and email has latency built into the system and then social latency built into it too, where it’s just like you don’t have the expectation of the fastest responses in the world on emails.
And so between the humans in the loop and then also the approach that we have to inference, which is we use lots of fine-tuned models, we use lots of different models and we use heavy reasoning on a lot of different steps. And so there are some tasks that we do where even without a human in the loop, it takes us n12 minutes to complete the inference. And that’s not an acceptable response time on text message, but on email that is totally an acceptable response time.
And so it gave us the ability to really focus on how do we get the result correct as opposed to how do we get a good and fast response?
Turner Novak:
Yeah. Just generally, maybe Howie or more broadly too, but what are you seeing some of these agents being specifically, really good at today, like different types of use cases, or on the other side, they still just can’t do? What are the limitations, generally speaking?
Austin Petersmith:
It’s really hard to get them to be perfect at anything, and that’s hard for us to kind of comprehend sometimes because it’s like you play with it and it works and so then you expect it to always work, but it’s just the 5% mistakes just don’t work because in any interaction there are a whole bunch of opportunities for it to have that 5% error.
And so it’s really hard to get perfection in pretty much anything. I think where the models are really good today is funny because I’m like, for our task even, the model, I’m very dissatisfied with. I mean, it’s like obviously we are living in an unbelievable era and it’s magic and create mind-blowing what we can do that we couldn’t do years ago, but I do not think that the models are capable of being an executive assistant even within the scope of scheduling today. I don’t think anybody could build it even if you had 1,000 AI researchers because there’s so much intuition and subtle nuance to the right step that needs to be taken.
But at the same time, they’re very good at speeding things up. So what we have for our humans in the loop is this kind of interface that allows them to do executive assistant tasks faster than anybody ever has before. So the tasks actually run, the models make predictions in a simulated environment, and the human, by the time they see it, they can see start to end what the model is trying to do and they can chat with it to interact with it.
So they can say, “You got the time zones wrong here,” and then they’ll see it resimulate right in front of their eyes. And that’s a pretty magical experience, where in January when I was our human in the loop and the only human in the loop that we had, and then Nicole on our team started doing it and it was just the two of us, but we were spending 30 minutes on these tasks that now we have people doing in 90 seconds.
And so where it’s worked really well for us is massive efficiency in still a human doing a lot of the kind of heavy lifting of the task, or at least spot-checking to catch the mistakes.
Turner Novak:
Yeah, and maybe that’s worth talking about because I remember it was kind of a big decision to kind of tear it all down, rebuild it, incorporate the human-in-the-loop element. What kind of went into that and how did you decide to do it?
Austin Petersmith:
We were doing the same thing everyone’s doing, which is prompt hacking, trying to get the models to be better, trying different fine-tuning approaches, RL. We were trying all the different things and we could get the numbers to move, but we could not have any line of sight to them, to the products being good enough that it never makes dumb mistakes, and dumb mistakes were just costing us customers.
It’s like people love the promise of it. They would start using it and absolutely love it, and then a couple of dumb mistakes and they’re just like, “I would rather just do this myself or pay for a full-time assistant.” And so we could see that chipping away at one basis point at a time to try to get to 100% accuracy was just not going to work.
And it’s not that we are the greatest machine learning engineers in the world, but we’re also pretty good at what we do. And we thought that if ... It wasn’t engineering resources that were the thing that was stopping us from actually climbing that hill all the way to the top. It was 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 a 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 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 get better at training the models, get better at doing the actual product experience, and then move faster in terms of taking on new types of tasks that are beyond what we’ve originally set out to do.”
So once we had that clarity, it still was scary. 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 in terms of recruiting the people, onboarding them and managing them. Three people on our team right now are at an offsite just planning the actual onboarding for the next cohort of people that we’re bringing on, and the documentation.
They’ve created simulated environments for people to 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 make them incredibly efficient and incredibly accurate at these tasks, and that was 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 so we have two different layers of the challenges in terms of getting the thing right, but 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 risks. And we started to see no one else is doing this. We inevitably are going to have competitors that 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 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 that scale for them to use. And so suddenly it felt like, “Okay, if it’s right, but that is the path to do this, then us doing it now makes us much more defensible actually.” And 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.
Turner Novak:
Oh really? I didn’t realize it changed the growth trajectory.
Austin Petersmith:
Yeah, last year, I mean we were waitlist only, so we were constraining the growth, but churn was a big challenge and usage retention, 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 the entire 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. His 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, 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, “It can fully manage my calendar.” And so, he leaned into it so hard. Yeah. And then since then, it’s really just been, I mean, yeah, been a steady clip of 30% to 50% 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 with the retention, the downhill ratio has been 30% to 40% 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 so, that’s really exciting because sometimes the MRR and the new customers can be harder. It’s like people will come in and try anything basically. And so, seeing that they actually end up using it every single day is just really, really cool to see.
Turner Novak:
Yeah. When you said down mouse, you said 30%, 40%, so what is that, two or three days a week?
Austin Petersmith:
Basically, what that tells you is that on a given day 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 so, for a lot of products where that can be just a red flag where you see it’s like lots of people are interested in it, lots of people might draw in their credit card, but the down mouse is 10%, which just means 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 interesting, but not actually that useful, or maybe they’re all just turning out really fast.
Turner Novak:
And then I think doesn’t, Waymo classically had this human in the Loom model forever and they still might, I don’t actually know.
Austin Petersmith:
Yeah. So, they do a lot of different things. Yeah, because Cruise was doing this 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. And yeah, I mean the model, 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 and...
Turner Novak:
In a self-driving car.
Austin Petersmith:
Yeah. So, 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. And it helps guide them toward the right answer.
And so, that has been 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, 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 and 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 the whole Sunset District, and then it was the whole city of San Francisco, and now it’s all the way down the peninsula and all over the place.
Turner Novak:
Yeah, you get the airport now.
Austin Petersmith:
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 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 and we can give more and more to the models to keep taking those things on. And that gives us a really nice innovation pipeline.
Turner Novak:
Yeah, it’s interesting when you just thinking about balancing that, there’s probably other cases where, I don’t know, I’m just making this up, logistics, emailing, copilot type thing or different industries where you see there’s a lot of these agents, but really should it just be super powered humans? I feel like there’s this weird almost trade off of people trying to make it pure software where in reality, you should be software super powered or supercharged human. I don’t know, I don’t know where the trade-off is on that, but...
Austin Petersmith:
Yeah, I mean 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. And so, it makes sense that it’s like can you build a fully autonomous AI accounting firm today? Probably not. But could you build a suite of tools that allow good accountants to be sanely highly leveraged, so they can be a hundred times more productive than they would’ve 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, and I wish there were more people doing it. And again, software people don’t love to staff up a human workforce instead of that. So, everyone is 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.
Turner Novak:
Well, I feel like we almost have this graveyard of people that have tried to do these in the past like pre-LLMs that haven’t worked. So, there’s almost a negative connotation, but I don’t know. I mean, I feel like we’re just going to keep trying and eventually someone will crack it.
Austin Petersmith:
Yeah, my last company I used Atrium, which was Justin Kan’s law firm, and that was their pitch was 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 if they had just stuck with it, they suddenly would’ve been able to actually streamline these lawyers to a crazy degree and they didn’t miss it by that much. I think 2019 that I was using them or something like that, and a few more years maybe could have totally changed it. Legal is definitely one of the areas where AI has become really, really valuable across the stack really quickly, because it’s just words and the models are pretty good at words.
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 the email based scheduling X.AI was doing this. And so, I think there are a lot of ideas that have been attempted in the past that suddenly are super viable today.
Turner Novak:
So, you think the thing you’ve cracked, just to make sure I get this right, is with the way that the Howie product works, you’re making a prediction on what you think needs to happen, 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 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.
Austin Petersmith:
Yeah. 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 timezone, 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, and so let me know if we need to actually move it or something.”
So, there’s all of those could be predictions that then by the time a human is in the loop looking at it, they’re able to 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 rerun this simulation with some new feedback and yeah.
Turner Novak:
Makes sense. Yeah, I’m excited to see now that you guys are... we can talk about the launch in a second, but you’re out there, people know you exist. I’m interested to see who can borrow in different categories.
Austin Petersmith:
Yeah, totally. And we’re 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 talking about it. Yeah, I mean that is an over simplification 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, but it’s also hard. It’s like 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 solves the problem on day one?
Turner Novak:
Yeah. And so, really quick just before we forget about this, I wanted to ask you the name Howie. Bold name and easy to remember. How’d you come up with a name initially when you started Everything?
Austin Petersmith:
Yeah. Dave and I, 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 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 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. But then there’s Siri and Alexa and plenty of precedent there. We knew we wanted a name that felt friendly, which is ambiguous, but 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. We weren’t going to buy the .com on day one, but we wanted to make sure it wasn’t a domain that had been actively in use for many years and would never be gettable if we did decide we want it. And a couple of others, I guess we weren’t totally sure on gender, but we did feel like a male name would be cool just because so many of these virtual assistants with names have had female names and it’s like, “Why not switch it up?”
And as we’ve gone with secretary as our branding, that also helps because some people did find the secretary thing to be a callback to an era that we don’t necessarily want to go back to, but it’s like, “Well, Howie is 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. And yeah, it’s just memorable. We had a bunch of parameters. We were building his list of names that fit those. And then Dave sent me this meme that is about a guy named How We Do It, and it’s like a screenshot of his Facebook profile with the Montell Jordan song, This Is How We Do It, playing in the background. And immediately, that was at the top of our list.
We were 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.
Turner Novak:
Yeah, I’m looking at this guy, it’s a selfie in a truck. He’s got sunglasses and a white beater on a black.
Austin Petersmith:
Yep, How We Do It. Yeah.
Turner Novak:
Okay, 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 made a lot of videos about this one.
Austin Petersmith:
Yeah, yeah.
Turner Novak:
I didn’t see this. That’s awesome. So, you launched. I mean you weren’t really in stealth because people were using it, you were talking about it, but you did the canonical launch video, which is actually pretty cool. So, maybe talk about what all went into that.
Austin Petersmith:
We had not announced our seed round, so we wanted to do that. For the longest time, we had a homepage that we built in three days really early on. And we had not updated it at all. And it had 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 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. It 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 the things that we launched was we announced the funding, we roll out a new brand that we worked really hard on that we think will carry us into the next era of the company. And we rolled out general availability. We still don’t have a free trial option, so you have to pay to use the product because that filtering has just always worked really well for us. So far, everyone who’s ever used Howie has paid upfront to do it and obviously, 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’d 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 customer stories that a video is going to be the way that we actually make it pop.” And so, the launch, we were planning for September and I think it was 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 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 in a day, this presentation that they did for us of 10 different ideas for videos, literally 10 completely different ideas all across the board. One was something with the, we get Montell Jordan to do, This Is How We Do It, and a bunch of different ideas. But one of them was the return of the secretary because the homepage was already saying Howie’s the people’s secretary. And so, we already were leaning into that. And the reason for that is there are 10,000 assistants in the world and every AI product is called assistant or co-pilot.
And secretary is a word that more accurately describes what Howie does like administrative tasks, like scheduling, not everything that an executive assistant does, which could be more 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. And 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.” So, we had very little time.
I think that normally these things take a bunch more time than this. But anyway, so 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 the casting call part of this would be one of the most time-consuming pieces. And so, they had her really quickly send a self-tape of herself reading the lines and we thought she was fantastic. And so, that was a really key piece. But then ultimately, it was like 10 days before launch that we signed the contract to do it. And so, then three days, later they shot it. They had to lock down the location and everything.
They found a great location in Toronto and we got delivery of the final video I think the night before the launch. So, it was all a frantic race to make it happen. But they totally delivered, everyone delivered, yeah, and it went really great. So, we were very happy with it.
Turner Novak:
What was the name of the firm you said you worked for to do that though? We’ll just give them a quick shout out.
Austin Petersmith:
Yes, newkid.services.
Turner Novak:
Newkid.services. Okay, cool. I’ll throw a link in the show notes if people want to check that out. Maybe what we’ll do, I’ll do a screen share and we will watch it.
Speaker 1:
It’s time to bring back the secretary. What? Hold on. Hear me out. We’re bringing back the secretary, not the job title, not the dress code. None of that 1950s bold. Hello? But the poise, precision, the prestige. Someone else is managing my calendar. You get a secretary, 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 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? Oh.
Turner Novak:
I loved it because I feel like a lot of the launch videos you see right now, they’re like, I don’t know, how would you describe the current meta of launch videos?
Austin Petersmith:
I don’t know. I mean, there’s been a lot of different ones. And I think that we wanted something that felt tied to the brand and to the product. We didn’t feel like it needed to be a whole product rundown because that is one category of product launch videos is just like you talk 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, that video is funny, but what is this? And 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 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 really happy with that conversion. It would’ve been great if it got 10 million views, but 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 it was just interesting enough that you go check out the website and then you get to see tons of customer testimonials. And we talk about the product more specifically in lots of ways there and ways have a brand that we’re really proud of there.
Yeah. So, I think that, I don’t know the other videos, I’m trying to think of other ones. I mean clearly obviously is completely crushing it and 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 the friend launch, which is mega viral on a scale beyond anything that at least in 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 focus it on the business and not 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 high production videos, but it’s just the founder talking about their thing. But we felt like it was cool to introduce a character who we now might end up using as a recurring character in some other videos potentially. And so, that idea was fun and I don’t know. Yeah, I think what I was most happy with is that it was a very short turnaround time and we produced something that feels really, really polished that one of... 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.
Yeah. I can’t remember what they are specifically, but they’re these quick cuts and cool camera movements and send. And the idea was just super fast pace and really high velocity. And the actress that we used was just so good. What I was envisioning from the script and all the ideas just was way less energy than what she ended up bringing to the table. So, it’s like 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 altogether, that would be the worst thing. But also if it went viral, but didn’t invert 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 of weeks since have been giving us tons of feedback and loving the product and the signups are still rolling in. So, that’s been really cool.
Turner Novak:
Yeah, it’s interesting in the sense of everyone knows what a secretary is or an executive assistant, so you don’t necessarily, to your point about how some people demo the product. If you just say, “Hey, it’s a secretary, it’s an executive assistant,” you’re just like, “Oh yeah, I know what that is.” And then I feel like the biggest question is, okay, but it’s AI. Does it actually work, right? I’ve used all these tools, they’re all sus. So, it’s like go to the website and it’s like, “Oh, there’s just a bunch of customer testimonials about how well it works. So, it’s like, “All right, cool. I’ll try it out.”
So, it’s an interesting, I think it’s almost like you need to position your marketing, depending on how mature a category is or how well the buyer understands, and then what their questions probably are based on 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 convert immediately? Is it like they need some social proof? Do they need some social proof? Do they need to know the price, et cetera? So ...
Austin Petersmith:
Yeah, totally. Yeah, I think that the social proof is just ... I mean, for anything, I think social proof is really key, and we are excited that we have so many awesome people that ... I mean, we had way more than we even could include, customers who just were thrilled to provide testimonials, and so that’s been really awesome, and I think that ... Yeah, it’s ultimately, our job is to just get people interested enough that they have an idea of 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.”
Turner Novak:
Yeah. I feel like social proof is very, it’s underrated, but also fairly rated. I think a lot of people, you kind of realize how important it is just to have a couple other people tell you just to get you across the finish line, really with anything, whether it’s buying product, even listening to a podcast. It’s like you see three people say like, “Oh, that episode with Austin and Turner, talking about Howie, 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.”
Austin Petersmith:
Yeah, totally. I mean, I think the reason that you don’t see a lot of social proof in many launches is not that they don’t think it’s useful, it’s that it’s really hard to have customers that love your product so much, that they’re out there amplifying. And that’s what made us so thrilled about the launch, was that the amplification, more than our investors, it was our customers who came out and were, in the comments, like the LinkedIn, especially the comments and the LinkedIn posts that we had are just, it’s just comment after comment of people talking about how much they love the product. And so that was just super exciting to us, that it felt like there was real substance to the launch 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 they’re proudly shouting from the rooftops about that. So we were really thrilled about that part.
Turner Novak:
And so when you do a launch like that, I remember, maybe I’m in a special group chat with you, where you’re showing us the ... I remember actually, I think I was at Disney World throughout the ... When you’re talking about filming, like how fast it went, I think you sent me a draft and watched it two days later, but it was finished or something like that, because I was at Disney World, I was a little bit disconnected. And then, when you’re launching a product like that, do you involve the customers like, “Hey, we just launched ... Tell us what you think of it,” 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?
Austin Petersmith:
There were 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 kind of 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. So when we were riffing on the script and the kind of concept, I was sending it to a bunch of different friends and getting their thoughts, but then, 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 ...” It’s like we’re at the editing phase. It’s like, “Do you have feedback on the color correction or something?”
So that was ... I mean, we did send it to a few people, though. One of the early cuts was 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 the brand and the webpage was definitely a ton. And Sophia Amoruso, 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, because with the brand, we also kind of went in a pretty novel direction, which is that it’s very people-first.
So we did a photo shoot with actual models that are 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 screenshots or kind of illustrations of features, and it’s just like all just features. And we felt like the experience we hear from customers is that they love Howie because 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 helping them with connecting with humans, whether it’s customers or investors, and there’s just 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 some of the folks that we sent the really brand idea to, they were like, “This looks like a makeup brand or something.”
Turner Novak:
It kind of does, yeah.
Austin Petersmith:
Yeah, it totally does. But we’re like, “Yeah, that’s fine.” We think our customers are awesome, and we want to showcase what we divide 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 some illustrated figures or characters or whatever, or just screenshots of Howie writing an email and ...
Turner Novak:
Yeah. If you did show screenshots the product, it’s like, “Oh, cool. A screenshot is superhuman, a screenshot of Gmail.” 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 a calendar and lots of blocks, and you kind of played around with animations as you scrolled of how ... Think it was kind of like scheduling, but again, I feel like to your point, it’s like a makeup brand. It does feel a little sexier, in a way.
Austin Petersmith:
Yeah, it just feels elevated. And that’s 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 a high-end luxury good that is inaccessible, but it’s also kind of baller. And actually, one of the analogies that I used with newkid, the agency early on was Uber, early days Uber, because it was at the time, you had yellow taxis, which were dirty. They probably wouldn’t show up if you called them, but they might, and they’re just all these things that are not great about that experience, and then there was 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 positioned the brand pretty, really kind of luxury and high-end, but it was also accessible, and it was called the “Everyone’s private driver,” and was their slogan early on. And so it was like taking this luxury out of reach thing, making it accessible, but still kind of baller. And that was one of the analogies that I had early on of what I wanted Howie to kind of stand for, is the executive assistant in this luxury thing that’s inaccessible for most of us, but we all know it’s pretty baller. And then the alternative is Calendly, which is a meme basically, how kind of inefficient, and it is the taxi, and 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 luxury, but it’s also accessible.
Turner Novak:
Yeah. Two things that, the way you said reminds me of, is when you get introduced to someone and they add their EA, some people, you might be annoyed like, “Oh, this person doesn’t have time for me or whatever.” With Howie, that jumps on pretty quickly, and it’s like response fast, but also, there’s almost like the power element of like, “Let me add my EA,” like, “I’m so ...” There’s almost this like you made it in life if you have an EA, or like a secretary. So it’s like, I kind of hate the word, democratize, but you’re democratizing and just allowing more people to have an EA.
It’s kind of like in between of sending someone a link, and then actually having a human assistant that you’re paying possibly six figures, all-in of comp, of taxes, social security, health insurance, salary, et cetera, and it’s interesting. I remember when I first met you when I was investing, I was like, “I don’t know, man. Calendly, like a better Calendly? Is this really an opportunity?” But I think in 2023, Calendly did 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 the opportunity is actually a lot bigger maybe than someone would think just from initial glance.
Austin Petersmith:
Yeah. I mean, to me, it’s like even just that ... Calendly is a great business, and it’s awesome, and it solves one thing really well, which is 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, and 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.
Turner Novak:
Yeah. Well, to the point of time ... It’s like time is money, right? That’s the Ramp slogan, “Save ...”
Austin Petersmith:
“Time is money. Save both.” I love that.
Turner Novak:
There’s probably some play on words with how we like, “Time is money. Save ...” I don’t know. You could say save both on Howie. I don’t know. Obviously, you can’t steal the slogan exactly.
Austin Petersmith:
That’s 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, but it’s like, “And just say both,” adding two words to it. 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.
Turner Novak:
Yeah. So you kind of mentioned there’s probably opportunities to expand over time. What does this look like? What does Howie 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?
Austin Petersmith:
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 what your company is going to look like when it’s doing $100 billion in revenue and you haven’t actually built something that people want to use for $10. And so we do really try to focus on what is right in front of us and, “How can we better serve the customers we have and end the day with more customers than we started with every day?” And that’s really where most of our energy is, but we do think about, “Where does this go?” And I think there are different paths.
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 consumer use cases, then professional use cases, but it’s just this super assistant for the individual, or you could see it being this 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 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 creating efficiency in a large team with the calendar. I don’t know, really, at this point. I really think the technology we’re building can work really well in both of those paths, and there probably are 10 other paths that I haven’t thought about. I think we’re excited about both. We definitely are excited about ...
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 kind of 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. And so over time, I think the main thing that is a clear North Star is we think that professionals of all sorts spend a ton of time on metawork, which is just work about work. So it could be scheduling, it could be setting reminders to follow up on something. It could be reviewing notes from your calls or anything like that.
There’s just a ton of things that all of us spend time on that is metawork, and there’s also a lot of metawork that 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 my coffee meeting this afternoon?,” and, “Do I ...” I don’t know. “I got that customer support email over the weekend, and I think I have totally dropped the ball on responding to that.” There’s all these things that just live in our head, and if how we can just be walking 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 metawork than building an assistant that does your actual job for you, if that makes sense, and anything that you could classify as metawork is probably something that we are intending to solve for professionals over time.
Turner Novak:
Okay. 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, how we could probably do for you.
Austin Petersmith:
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 we’ll 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. There’s enough demand in the Google ecosystem that we haven’t been in a huge rush, but we also get emails literally 10 times a day, asking us for Microsoft Outlook support. So we’ll unlock a lot of potential new customers, and so that’s really valuable, but ...
Turner Novak:
I mean, Outlook is enterprise. When you get Outlook, you’re going to start signing those 1,000 seat, 10,000 seat deals, so that might be valuable.
Austin Petersmith:
Yeah, totally. I mean, there’s tons of market opportunity there. We don’t really have a good offering for 10,000 people to use Howie today, but as we go, yeah. I mean, we get interest from any number, like company size, industry. People are reaching out, and we just have had to kind of 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, and that’s just limiting because we want to serve many, many more people than that over time, but it’s allowed us to have 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.
Turner Novak:
Yeah. And actually, I meant to ask this earlier, but I mean, you mentioned we’re growing 30%, 40% a month. What’s the current state of the business? Is there a public, or even a private ... You’re only saying it on this podcast. What’s currently kind of the size of things, kind of the state of everything?
Austin Petersmith:
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, Howie’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 in the investor updates. We just have been growing.
Turner 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 what.
Austin Petersmith:
I know. Yeah, I think those are the main kind of public numbers right now.
Turner Novak:
Okay. So actually, going back to the early days, you talked about 2015, the Slackbot or the Slack channel. You kind of skipped to have 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 Calacanis, and you said, “People are always curious.” What was that like? And I’m also curious, what was that like working for Jason?
Austin Petersmith:
Yeah. Everyone always wants to know ... I very regularly meet people who immediately, when they learn that I worked for Jason, they want to know.
Turner Novak:
He’s good at what he does, obviously. It’s not like an accident.
Austin Petersmith:
Oh, yeah. So he’s a really close friend. I was going to be like, “He’s a fucking moron.” No. So Jason and I definitely would have pretty intense arguments and things, and 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 them, 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 the manicured version of ourselves. And 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 kind of ... Back then, this was like 2016, he was studying constantly.
I would get in his car, and he would sit there and make me watch 30 minutes of Charlie Rose interviewing someone, or Oprah interviewing someone, or Howard Stern interviewing someone, and he was literally studying the tapes of these interviews. He’d watched 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 ... Once the All-In Podcast came out, and he had to serve as this pretty challenging role as moderator for a bunch of really powerful personalities that have ...
Like all want to hear themselves talking, 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. So that’s all cool. And yeah, I mean, it was interesting. He definitely ... As you would expect, if you followed him online and 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 experience and 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 he’s definitely a person who has deep loyalty, and I’ve felt that. And so it’s cool that from the first day that I ever met him, I have felt like he truly has my back. And so as much as he could be a dick or he’s polarizing, there’s all sorts of things on mind that I 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 you don’t often find somebody who you feel like actual real loyalty from and to, and so yeah. So he’s a good friend.
Turner Novak:
I mean, did you learn a lot about media from him because he really runs pretty interesting, pretty like a media company.
Austin Petersmith:
Yeah, totally. It really is more of a media company than anything, and yeah, a ton. I mean, he’s been doing it forever. I mean, he was talking print magazines in New York in Silicon Alley, something. I can’t remember what it was called, but-
Turner Novak:
Yeah, back in the ‘90s, right? Like late ‘90s.
Austin Petersmith:
Yeah. So he’d been doing this forever, and he knows everybody, and he’s seen so much. And so that is one of the things that I started to learn, is I would often think he didn’t know what he was talking about and sometimes realize that I was right, but more times realize like, “Oh.” Actually, he’s really done this shit, and he knows what he’s doing, and yeah. So with media specifically, I really think he has a good grasp on how to do it.
And, I mean, even just, he was investing in video content for his podcast at a time when nobody ... Everyone was just doing audio only, and he would have cameras for every single podcast interview in person, never remote, and never audio-only, and that was just ahead of the curve, and now he has a back catalog going back 16 years or something of these video podcasts, and so yeah, all sorts of things like that, where it felt like he had a pretty good grasp of 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 you see a lot of people kind of try to start a podcast or start some sort of form of media, and then just when it doesn’t become the next big thing and three weeks, then they just kind of fizzle out and abandon it. And there’s a lot of value in just continuing to do the next episode and the next episode, two episodes a week, you just keep going, and that over time really does compound. And so the determination is definitely a big one too.
Turner Novak:
Yeah, it’s hard. I mean, I’ve been doing my podcast for two and a half years at this point. It’s almost unpredictable. I’ll be like, “Oh, this one’s going to do so good,” and then I’ll post it, and it’s like the worst one of the year, or it’ll be one ... I mean, honestly, when I go back and look at the data, I could not have predicted what the better episodes would’ve been.
It’s like with all content, even with Twitter. Some of my most viral tweets, they got 10 million views. There’s a typo because I posted on my phone really quick and it did autocorrect. I didn’t realize it. And then, there’s some, where you spend an hour on it, and it gets 1% of whatever what you thought it was going to get.
So it’s like a lot of it’s just like a volume. It’s just shots on goal. It’s just staying in the game, keep putting stuff out there. I think that’s just generally the thing with, really media, or the internet, or content on the distribution side, is a lot of these algorithms, the way they work, there’s almost unbounded upside, right? There’s 100 million people that might potentially see the content, and it’s just 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, say you post once a month 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 a goal you have, the more surface area chances that people see your stuff. I guess you’ve got to balance not being annoying also.
Austin Petersmith:
Yeah, I mean, that is tough.
Turner Novak:
Yeah, so just post about what you’re doing, tweet about what you’re doing. Put content out there that’s natural to you, that’s easy, that fits in with what you’re good at and what your unique advantage is. And I don’t know, I feel like not enough people think about it that way.
Austin Petersmith:
Yeah, totally. And I mean, it applies to anything. Building a product and building a business, it’s like you can get so distracted in where you want to be or in how difficult the challenges in front of you are. And for us, every day of building this company has been just like, can we get one rung higher on this ladder? I mean, we chose a problem that’s definable of scheduling. And so it’s like, early on the only thing was 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 it ends up 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? Just doing that, then the compounding starts to happen. And so it can really apply to anything, I think, the idea of you just need to move forward a little bit every day.
Turner Novak:
Yeah. So speaking about compounding, I know you’ve had just a pretty steady, continuing to grow product. It’s interesting when you think about how someone maybe discovers Howie. It’s probably in their email inbox. That’s maybe the place they discover it. Do you remember, how did you 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,” and it took off from there? What was the process?
Austin Petersmith:
Yeah, the first, so we put up a wait list early on, and people started to sign up. And I had it in my Twitter bio, and there were a few people early on who started using it and then tweeted about it and that would lead to... Because at the time the product was not very good, but it was good. There was at least 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 eventually they would run into the issues.
So that was enough to validate the demand, and then the wait list started to grow. And so then we would look at who’s on the wait list and go reach out to people. A couple of the very first customers we ever onboarded are still using the product today, which is remarkable because they really rode through the... I mean, some of them who are friends, but that’s still remarkable. Alex Cohen, for example, used it all the way through and was not dissatisfied with the old product, but then once we rebuilt it was just like, “This is mindblowingly better, and 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.
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 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, but 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 a marketing campaign or whatever else we want to do, but ultimately it’s not trying to catch lightning in a bottle, it’s just how can we reach a few more people today.
Turner Novak:
But you were telling me the other day about you had this really interesting strategy of doing your pitch deck that is unique, simplifies the process, but you think it works pretty well. What’s your strategy for making a deck?
Austin Petersmith:
Yeah, so I’ve looked at a lot of DocSend metrics. 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. They’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 a hundred 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. And so more slides with less information is just 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, but the shortest possible thing. Have a narrative arc that pulls people through. So I don’t love the standard templates of problem, solution, whatever. You need to hit all of those things, but you should have a story that gets somebody to want to go to the next one. And then again, put an amount of information that can actually be digested in three seconds because 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 and really read through each slide slowly, but to even get the chance for the slow one, you have to have passed the three-second test.
So don’t worry about, I’ve seen some people recommend, “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 a ton of content into 10 slides. You 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. 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.
Turner Novak:
So instead of just thinking about it as 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.
Austin Petersmith:
Yep, a hundred percent.
Turner Novak:
The next set is like, yeah, it might be a couple screenshots of the way you solve the problem or sentences on how you solve the problem and however you need to find the market opportunity. Maybe it’s a couple slides. And again, it’s just really because to your point, people don’t read. A lot of the times, there’ll be tons of text everywhere, and you just read the header or what’s the most bolded image or thing that stands out.
Austin Petersmith:
Nobody 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 in punchy, short sentences that actually tell a story, and then people will actually read it, and otherwise 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. And 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’ve got to 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.
Turner Novak:
Yeah, that makes sense. It’s a good strategy to think about. And you’ve mentioned before in the past just when 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. Why do you think that’s the case? Don’t you want growth? You want ARR to go up super fast, and you get a higher valuation, raise money, right? Isn’t that good?
Austin Petersmith:
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 growth hack up 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. And I’ve done all those things in the past, and I’ve experienced building a product that has all the growth levers 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. And so we’ve never had time to build out. We literally don’t even send emails. You sign up as a new customer, and 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 sign up, and we’re going to add trip campaigns that go out and we’re going to add more user education. 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. So 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. There’s no bookmark that you save in your browser there. Howie doesn’t just email you... Actually now Howie does email you proactively for conflicts and things, so we’ve, I guess, added some of that proactive stuff, but that even six months ago didn’t exist. And so there is, I guess, some proactive things, but for a while there was none. And so the retention, the word of mouth growth, the usage numbers, and all those things looking so great was really validating for us because we are in the ground truth. We’re not tricking people into coming back, and we haven’t optimized. We’re not pulling any of the levers 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 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. But 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.
Turner 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.
Austin Petersmith:
Yeah. I mean, the best products in the world grow themselves. Why should you have to spend a bunch of time on the sharing functionality or the referrals, or why should you even have a referral program for a product that’s in the early stages, pre-product market fit? Why should you spend any time on that if the product is not so good 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.
Turner Novak:
Yeah, and I guess too, the way that the product works, 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 as like, “Oh, what’s this Howie thing? Howie.ai or howie.com? I don’t know what URL.” Or some of them might obviously use the custom URL, so maybe they don’t even see it.
Austin Petersmith:
Yeah. 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. But the person went through the whole scheduling experience, and I think they had had to reschedule the meetings. There’s some tricky element of it, and the person was really impressed. And they sent an email to the Howie customer and to the white-label Howie saying, “Do you have any friends? I really need someone like this to do my scheduling.” So they thought it was a human and were trying to hire the friend, 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 literally the same assistant. You don’t need one of his friends.”
Turner Novak:
No way.
Austin Petersmith:
Yeah. So it does happen for sure, sometimes through direct word of mouth or everyone’s just always talking lately about, “What AI tools are you using?” And so I hear these stories of, “I was at this coffee meeting, and my friend asked me what AI tools I’m using. And I said Howie, and they said, ‘Wait, like the thing you used to schedule this coffee meeting?’ And I said yeah.” And so it happens that way where less than... Again, we don’t put 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, so we just don’t want to dilute the product experience for the sake of a growth hack.
Turner Novak:
Yeah, that’s always good. And when I first met you, you were living in Bend, Oregon. I think you are in Seattle now. What’s the significance of living there? Shouldn’t you be in San Francisco? You’re building an AI company.
Austin Petersmith:
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 10 years, and it does definitely help that we have 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. We lived in different states at the time, so 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 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, there’s more in SF than anywhere else. But the challenge that friends of mine are having is 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. And 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 it cool. And because of those companies also, there’s a ton of tech talent. There’s less engineers that are excited about startups. We got an applicant from an engineer a few weeks ago who is at Microsoft and has been at Microsoft for 31 years, and 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.”
Turner Novak:
Who knows? They might be. Hey, they’ll stick around for 31 years at Howie. That could be good.
Austin Petersmith:
That’s true. That’s loyalty, yeah. 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 stand out in that regard, and there’s still plenty of tech talent. And then most of our investors are down in SF, but we traveled down there and know lots of those folks already. And so for us it’s working really well, and it’s fun to be building in a place where we feel like we can really be on the map, especially as we grow.
Turner Novak:
Yeah, makes sense. One other question I wanted to ask you, but I know you do... It’s not like your full-time thing, but you do some angel investing. You actually work with your brother. You guys have a small fund. It’s like an angel fund. You have a pretty interesting, pretty good rap sheet. What’s the greatest hits on the Austin and Stu Angel portfolio?
Austin Petersmith:
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, but because those investments were good, I had track records. 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 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 could invest other people’s money.
And so first company 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 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 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. We knew some of the co-investors who were pretty impressive names. And so we made that bet, which is Lattice and now is doing, I’m not even sure how much, but well over $100 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 was progressing from there. And that was incredible, so I was just like, “Hey Rahul, can we please put money in?” So we did that one.
Then a couple of years later, Mercury, I had started my company Capiche, and I had had really frustrating experiences with SVB when I was working with Jason and we were using SVB. So I started searching around online for, are there modern alternatives to these banks, and found a post from Immad who said, “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 building the thing, but yes, you can if you want.” So I signed up, and I was Mercury’s third customer. And I got to see, I have these email threads from, it must’ve been 2019, where I was reporting a bug to him because I was trying to get a wire. I can’t remember what it was, but something, and it’s like 10:00 p.m. on a Saturday. And then 20 minutes later Immad’s like, “I just pushed a fix. It should work now.” And so again, 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 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’d be insane not to invest, and now I know you’re raising. Can I please put money in?” And so we did and then we raised the first cough drop. We call it cough drop capital. My last name is now Petersmith, but originally it was Smith. My wife and I merged Peterson and Smith to make Petersmith. So Stu and I were the Smith brothers, and there’s like a 150-year-old cough drop company called Smith Brothers Cough Drops. And so the name cough drop capital is a funny homage to that. 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. We raised the first fund, which is about $1 million and still has a ton of active companies that are doing great. And then the next fund’s $3 million and is currently being deployed today.
Turner Novak:
Nice. And it’s pretty small checks, right? Like 25K, 50K.
Austin Petersmith:
Yeah, yeah, exactly.
Turner Novak:
Nice. That’s easy to slot into a cap table.
Austin Petersmith:
Yeah. Today I have pretty much zero time for investing, and so it’s mostly like sometimes customers of ours that are building cool things, and I’m like, “Hey, can I put 25K into this thing?” So it’s the deals that fall in my lap are where I’m focused. I’m not going to YC Demo Day or going out and taking pitch calls with founders. It’s just cool stuff that I’m using or just excited about.
Turner Novak:
Well, that’s the thing. That’s what everyone always says why founders are good angel investors. They’re just in the trenches. People are asking them for advice. They’re using new products or trying things. People are trying their products. So you just see different stuff than some country club guy who is retired and maybe was an early Oracle executive or whatever. It’s a totally different world.
Austin Petersmith:
Yeah, yeah. Totally.
Turner Novak:
Well, cool. This was a lot of fun. Thanks for taking the time to do it.
Austin Petersmith:
Yeah, thank you so much for having me. This was awesome.
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