Episode 2: Bots to date for us. The future of love?

Picture this – in the future, an AI bot will learn you and your preferences. Fancy dinner or dive bar? Tall or short? Funny or serious? The bot will browse the dating apps, start conversations, flirt, and set up dates for you. It might even predict your compatibility score with a future mate. An episode of Black Mirror? Nope. It’s tech already being developed on the fringes. You might be talking to a bot on one of the dating apps right now, and you don’t even know it. Conversational artificial intelligence is getting intimate. Entrepreneur Shane Mac has been building this technology for years. Now he’s talking about it for the first time, and it’s raising all sorts of ethical questions. Do you know if you’re talking to a person or a bot? And is it ok for machines to act human when it comes to our hearts? First Contact explores the blurring lines between love and algorithms.


Shane Mac: It had this moment where you thought, if I unleash this to the world, could it do harm? But could it also do great? And we had this like very big debate with ourselves.

Laurie Segall: And it’s not public yet?

Shane Mac: No, because we-we’re scared to put it out there. 


Laurie Segall: Let’s talk about the future of dating. Because I think it’s gonna get a bit weird. Everyone’s on the dating apps these days – hinge, bumble, tinder – that’s a good way to find someone.

But I think a lot of us are dealing with some of the same issues created by tech – Infinite options but trouble with connection…

This idea that you match with so many people … but there’s a lack of real human connection. Accountability. People are  almost becoming pixels. 

With that in mind I want to take you to the edges – tech being developed that’s pretty controversial – even the guy who created it doesn’t know how he feels about it.  It’s a bot that can respond to you on the dating apps – it will start the conversations, engage in witty banter. Arrangethe dates.

Weird? Totally. Dishonest? Yea- and honestly  I don’t know exactly know how to feel about it but I think there’s some really interesting gray area to explore here – there’s something fascinating about this moment that he’s touching on. 

Oh yea – he is Shane mac he’s a technologist whos built out bots and conversational artificial

Intelligence for years – and he thinks a lot about how machines interact – and how they can feel more human. But what happens when you apply that concept to the future of love?

I’m Laurie Segall and this is first contact.


Laurie Segall: The podcast is called First Contact. and there’s a reason for that.The reason for that is because I’ve been in tech for basically 10 years, which in tech years is like, 100 years, right?

Shane Mac: Yeah, I’m basically like 49, and I feel like I’m 49.

Laurie Segall: Yeah.

Shane Mac: Like, I’m tired.

Laurie Segall: We named this First Contact because I, we want to talk about my first contact with people that came on. And so, I was trying to think of my first contact with you, um, cause we have met before.

Shane Mac: We have. It might’ve been at a Charity Water Ball, in New York.

Laurie Segall: Mm-hmm (affirmative). Because here’s the thing Shane, I went, um, back into my text messages, you were in my texts as, hello there. Like, I, that’s embarrassing, but like-

Shane Mac: That’s 2009.

Laurie Segall: Yeah, like, well actually our texts date back to 2012, and I just have you in my phone as, I mean I can’t believe I’m admitting this, but I just have you in my phone as, hello there. I guess, was that, that was the name of your old company?

Shane Mac: It was just a product I’d built, uh, that let people build websites for companies.

Laurie Segall: Mm-hmm (affirmative)-

Laurie Segall: December 7th, 2012, “Hey Laurie, Shane Mac from Hello There, it wouldn’t let me leave a voicemail”…that’s probably because my voicemails always full, nothings changed, um-

Shane Mac: This is real?

Laurie Segall: Yeah, so-

Shane Mac: I-I’m afraid of where this is fucking going.

Laurie Segall: …all night to chat, hm, okay. Anyway, so that was our first contact, dating back to 2012-

Shane Mac: Wow.

Laurie Segall: …and you’ve had a very long career since, um, and you’re still in my phone as Hello There.

Shane Mac: Hilarious.

Laurie Segall: I brought you in because of a woman named Zenia, she’s a mutual friend of ours, we both know her.

Shane Mac: Yep.

Laurie Segall: And she said something to me that I thought was like, one of the most fascinating things a tech person has said to me. We were doing an interview in San Francisco, like outside at some fancy place, and she was talking about artificial intelligence, and a friend of hers had passed away, and using all his personal data, and text messages, and, like, anything he put out there publicly, she had re-created a digital version of him…a bot of some sort, um, that she would like…it was almost like a shadow of him, that she would still talk to. Which was like a crazy concept at the time. Um, there’s like a Black Mirror episode that feels very similar to this, and she would be texting with, like, the Roman Bot.

Laurie Segall: So we’re having this whole conversation about the future of AI, and she said one line to me, and htis is how as a reporter as a journalist how i always end up doing different episodes in like i go off into the world and do a whole different story based ons omething one person says to me in an interview and this is how i think i’ve come to you.  She said, “Well in the future, we won’t even date on dating apps, we’ll have bots to date for us, like, they’ll just date for us, we won’t even have to swipe”. I was like, hm, I wonder if down the line, that will happen. So that brings me to you, Shane Mac.

Shane Mac: Here we are.

Laurie Segall: Yeah, and um, that’s gonna happen right?

Shane Mac: For sure. It’s already happening.

Laurie Segall: And-and so, tell me, and-and it’s happening because you’re doing that in some capacity, before we kind of get into that, let’s talk a little bit about you. you’re obsessed with Bots.

Shane Mac: I am now.

Laurie Segall: what about them?

Shane Mac: It wasn’t my first love. I was obsessed with messaging, and I really loved the idea that I should be able to text people and businesses the same, and the future would… be all lived within messaging, not calling or doing a crappy website or downloading an app. And then, my co-founder was the founder of Geek Squad, Robert Stephens. And, he came to me and said, “Hey, the future is not messaging humans, the future is messaging Bots”. And I was like, “What do you mean?”. And he’s like, “Well the future is about language talking to systems”.

Shane Mac: So he was like, let’s just hack Great Clips website, and I’m going to build a text bot that allows me to say, I want to get a haircut today, and it’ll go fill out all the stuff for me automatically on the website and the bot will respond back and say there’s an opening in 12 minutes, 14 minutes, 19 minutes. And we built it, and this was like 2013, and we went in and Robert’s name was on the screen and it said, Robert Stephens, 12 minutes. And he’s like, this is the future. And, it’s going to remove all this software in the middle, and so, then I became obsessed with the mission that, bots will create the next wave of the Internet which I think is about getting us off the Internet.

Shane Mac: The last decade was about getting us on the Internet, and I think the next wave is about getting us off of our devices.

Laurie Segall: like in what capacity?

Shane Mac: Cause, if you start with today, you start with letters to make words, words to make meaning, and meaning goes to be an intent. But if you go to tomorrow, I think we start with intent, you’re like I wanna get a haircut, and the bot goes and makes it for you. And it learns about you and knows your preferences, and knows how you talk to everyone else. It watches…in dating context, I look at where people always have friction and get kind of, uh, annoyed, and I’ll listen to people on dating apps, and they’re like I have an inbox full of tons of people, we all say the same shit, and it’s just an endless banter and I can never remember who to follow up with, and then I’ve taken to my text messages and I don’t remember a name, don’t have your na…named Hello There, and you’re like, I don’t fucking know who this person is.

Shane Mac: And, I listen to that, and I’m like okay, so that’s not the future, it’s too much friction, and it’s like causing people anxiety, and I think the bots will handle all of that.

Laurie Segall: And can you, just for our listeners, um, explain the most basics of like, what is a bot? 

Shane Mac: Yeah. it’s just a piece of software that can communicate with you. And whether it’s on Alexa, that would be a bot. Whether it’s, um, in uh, text message and it responds back and says, “Have a great day”, and it’s a computer system, not a human. That’s a bot. Or if it can talk to systems, like we have bots that we’ve built that can, book haircuts, and book appointments or book a flight or do anything like that.

Laurie Segall: And your company, Assist, essentially built kind of this platform all for this.

Shane Mac: Yeah, exactly.

Laurie Segall: So much so that Facebook, um, kind of called on you. I remember when Mark Zuckerberg, um, was up there, and Facebook launched bots, like Zuckerberg is up there talking about 1800-Flowers. Facebook has this developers conference, for folks who don’t know, um, they have this like developers conference once a year where like all the Facebook executives get up there, and they talk about like their biggest things that are coming down the pipeline, and it’s like a very big deal for Facebook. Um, and they kind of set the stage. And I remember Mark Zuckerberg getting up there, and he’s like, you never have to call like 1800-Flowers again. right And, it’s because like there’s like a bot right, or something for it-

Shane Mac: Totally.

Laurie Segall: …and that was powered by you guys.

Shane Mac: Yeah, we were the first bot partner to ever launch.

Laurie Segall: Right.

Shane Mac: And we got a call 72 hours before F8, we didn’t know it was going to happen, and they said, “Zuckerberg wants to know if the CEO will care at 1800-Flowers if he makes fun of them”. And the CEO is like, “No, it’s amazing, let’s do it”. And he’s always been very progressive and he built his company off being the first company in the world to sell on a phone number. And then he was the first person to sell on the Internet on copy serve in 1993. And so, the fact that they were the first to launch with us to do bots, that makes sense, and it was cool.

Laurie Segall: And so you sold …you were acquired, assist was acquired. Um, and this is where things get interesting, right? Because like I think, um, you know, we’ve heard now about bots like for all these big companies using them, especially customer service bots, and all this stuff. But like things are getting really, uh, this is where like I light up, right because like-

Shane Mac: Me too, I love this part.

Laurie Segall: Things are getting kind of weird, right? Because, like, now they’re going to be used in all these different ways, like, this is the stuff that no one is talking about, there’s a whole other use case of bots, and you started thinking about it,, um as it pertained to, like, our personal lives, right, in dating. And there’s a problem and hte problem is that there’s so many options, it’s really hard. All of this is happening kind of simultaneously.

SM: Yeah

Laurie Segall: So you have kind of somehow, Shane, thought about bot use for dating apps. How did that come about?

Shane Mac: Yeah. So, I’ll give you the business answer and then, like, my personal answer.

Laurie Segall: Okay, okay.

Shane Mac: The business answer is I’ve actually always been very interested in the space. Um, and I was, like, the swipe is commoditized, so all their business models are built on connection. But the connections now infinite, like, it’s not that you can’t get connected, cause everyone’s on them, it’s become mass market and there’s no more stigma. And so now, everyone’s connected-

Laurie Segall: Yeah we literally…there’s like, so many connections you don’t even know what to do with them.

Shane Mac: Exactly. So they’ve nailed their business model so well that it has no value.

Laurie Segall: Hmm.

Shane Mac: So now you have endless connections, but that’s how they make money. But if I don’t need to use specific apps or pay them to have more connections, then the question becomes, if-if swipes were like how you walked up to someone in the bar and you judge them, you get to look at a photo and swipe left and right, I think the future is actually the language of the bot. Um, that is what I was like, oh, the first response is actually the new swipe. The words are the swipe. That’s how you get a response, cause everyone that I talk to sends messages and never hear back, so then the way that you send messages and how you communicate effectively. Do you have any wit? Are you funny, or are you curious, are you asking specific questions? All those types of things, stuff that I would like to think about and just, like, how do you get people to be more curious and more specific in their questions asking? I was like, if I can teach everyone how to do ask better questions, will they get better answers and will they get more responses?

Shane Mac: And there’s the new business model based on words, not on swipes. That’s how…and then I was like, maybe.

Laurie Segall: Okay, so now getting the personal answer, because you’re also a dude who sounds like you’re on the dating apps and like, I know every founder tries to fix a problem for himself, so, were you just like not getting responses.

Shane Mac: No, not at…it actually, if you, take Hinge right and. I love what Hinge did. They make it more personal, you have to write a personal message to a piece of content, that takes so much time. And so, I’m looking at it, and for me, I’m just always optimizing, like, time, and I’m like, wait, I’m writing the same type of message for the hiking photo jumping at the top of a cliff, for almost every single one, um or a piece of food that someone has, or they have the picture on the boat, or they have a dog, like they’re all kind of the same. And it’s kind of sad, and I was like, shit they all look the same in this profile format that Hinge created and it takes forever to literally type a thoughtful message, over and over again.

Shane Mac: And I was like, I wonder if I could create a bot that would watch how I communicate, and optimize it based on if people respond, and over time be better at writing, and also use the community so if other people are using different language, I would learn… like you know you could search it on the Internet, you can search “What are the top 50 things to say on a dating app?”. But when it’s in your keyboard, and it’s part of your bot, and it’s part of your conversation, it’s like there at the moment when you’re sending a message. And you can then send 50 messages in a minute instead of 50 messages in a day.

Laurie Segall: Oh my god. So, take me to it, when did you start doing this?

Shane Mac: Uh, I built it about a year and a half ago with a guy named Stefan.

Laurie Segall: Okay.

Shane Mac: Because we were working on at work, how to predict, uh, language based on feelings. So the bots we built at work, what the business wants to know, is is that person mad, sad, angry, anxious? And we can actually tell, based on the language, how the persons feeling and tell the brand, hey, this persons really mad, or this persons really anxious or really sad, just based on their words.

Shane Mac: So when we were designing these keyboards and stuff, I was like, I wonder if you can use this in your personal life. Like, if I can understand how someone feels, I can respond in a whole different way to anybody else.

Laurie Segall: So how does that apply to the dating apps and your bot?

Shane Mac: Because when they’re having the conversation, you can understand and change the responses based on the language that they’re using.

We’re going to hear more from Shane Mac right after the break.

Laurie Segall: Okay, so tell me…take me to the first time, this is a year and half ago, what exactly did you build?

Shane Mac: Uh, it’s a keyboard that does suggested responses based on, uh, the context of the conversation. So, opening lines, if you’re into banter, or if you’re just kinda general questions based on the way they’re responding, and then also based on how to ask them to get off the app and go on a date.

Laurie Segall: Okay. So, give me…how-how did it feel the first time you used it, like tell me, give me an example. What did you do, like, the first time you used?

Shane Mac: Honestly, –

Laurie Segall: Because by the way, like, for your listeners, like, I-you helped me do this, and like the first time you use it, it’s insane.

Shane Mac: It blows your mind.

Laurie Segall: It-it actually, that’s what I’m like, I don’t mean to be whatever about this, but like it actually blows your mind. So let’s not talk about this in way that’s like, being so whatever, like it’s actually mind blowing, and it feels, it’s all sorts of weird feelings. So take me back to you a year and a half ago, like, you built this technology, you’re on the dating app, like, you have keyboard which kind of does all these responses for you, like what goes through your head?

Shane Mac: At first, I was-it, there’s always moments of technology where you uses something and you’re like, holy shit. And that was how I felt when I used it. I was like, oh wow. Like, this works. Saves a ton of time. Um-

Laurie Segall: Do you remember what you said? Or what your bot said, I guess?

Shane Mac: Uh, the bot probably said something very specific about…what’s your favorite dish in the world, may I take you there if we can make it past 17 and a half dates? Or something funny like that.

Laurie Segall: And the girl responded?

Shane Mac: Or, where’s the photo of that hike, literally gets a response every time, and it’s like so simple and dumb, but like, it’s programmed in the bot for any hiking photo. And I…this was the terrible one, I literally came back to my inbox one day, and there was like 15 response of like, Yosemite. It was just like all the hikes, and I was like, oh my god I feel terrible.

Shane Mac: Like that’s when I felt, I was like, I don’t know if this is good or bad, I don’t know, I don’t know what this is gonna do, like, uh, I just was like, this works so well, and it saves a lot of time, and everyone I show it to is like, I really want that keyboard.(laughter)  Like, everyone, and I’m like uh. So we didn’t actually put it out in the public, because I didn’t know what was going to happen with it.

Laurie Segall: Right, um, so okay this was a year and a half ago.

Shane Mac: Yeah.

Laurie Segall: Um, and-and so you have like this whole keyboard that has, it has categories cause, um, I know because you installed it for me, But,, it has pre…it has categories like banter, opening lines and, and, and you actually have to go in and press them, so eventually the idea would be that, the bot just does it for you?

Shane Mac: Totally. Actually, the whole idea started, an idea I had called Witty Bot. So I wanted to build a bot platform that…for dating apps, but both sides were bots, and everyone knew it and you would watch your bots communicate. So you would watch my bot go against Laurie’s bot, and we would see if it got passed each others witty banter, or whatever, cause it knows based on past conversations what you like and what you respond to and what you don’t. And so, if you think of eHarmony as 80 steps to get matching, so you go through 80 steps so they can match you. Well now you’re matched instantly, because the dating apps have made that a commodity. So now it’s, why doesn’t the 25 conversations, be able to just talk to each other and see if you’re  be a good match based on how you communicate.

Shane Mac: And that’s actually where the idea came from, and I was like, but it’s too early for that, it’s too creepy whatever, I’ll just build it for one side of it, so I built it so someone could use the bot and the other side doesn’t know. And that’s where I think it’s another scary part, is that the other side doesn’t know that its automated and doesn’t know its a bot.

Laurie Segall: Right, and i want to get into that because i had a very interesting experience with the other side not knowing. Like dot dot dot i came clean and i’llt ell you what happened later. I think like this idea, this like voyeuristic, like our bots are…this is like where we get really Black Mirror, right?  the idea behind this technology, these bots are a reflection of us-

Shane Mac: Totally.

Laurie Segall: They get to know us, right? You’re the technologist here, right, like-

Shane Mac: For sure, it learns every time.

Laurie Segall: It learns you over a time, and so it would learn your likes and your preferences. So the idea would be,that  it would learn you, and your…my bot would learn me, your bot would learn you, and then they would potentially have a conversation and in then this very voyeuristic way, we’re watching our bots figure out, um, based on data and, and the past if we would be compatible?

Shane Mac: Totally.

Laurie Segall: Oh my god. I mean, how do we feel about that? And also, do we trust our bots? And also even trust ourselves? I don’t know, I mean, I’m not sure, I’m confused.

Shane Mac: I mean, right now we’re just swiping on photos and it’s even more voyeuristic. Why not let it be more about personality.

Laurie Segall: Right.

Shane Mac: Uh, and, I think it’s scary now but its like, online dating was scary when it first started. Um, but I look more at where people see the pain points, and I watch everyone hate doing the endless banter in the inbox with a bunch of strangers that you don’t know if you’re ever going to meet, and its like and endless, it-it actually feels endless which is a whole other conversation or your problem. And I think that the-the bots can get us off the dating apps. And I think that it can be better at match making, more specific and know more of what you like.

Laurie Segall: Right, your whole thing is,, it can r-reduce the friction of having to have these whole conversations, get us offline and put us in real life.

Shane Mac: Totally, cause I also make appointments with this stuff, so the dating apps will be created as fully bot driven, and you just have a conversation with the bot like she did with her passed away friend, and that becomes the thing that it knows you like, and then that can have a conversation with anyone else’s bot.

Laurie Segall: Um, so let’s go to you personally. So have you…so how many bot dates have you been on,like and I…I say bot dates, I mean like dates that you, your bot has kind of set up?

Shane Mac: More than one, less than 20.

Laurie Segall: Okay, um, okay, and so-

Shane Mac: I was with a guy

Shane Mac: And I remember showing him the keyboard. And he was like, it has this like, the first time you see it’s like, what is that? And he was like, what is that thing? And I was like, watch this. And I just started sending the photos, and this lady was like le-leaving a wedding at like 4:00, we were in the Mission in San Francisco. And she responded instantly. And he was like, holy shit. And I was like, I should go on the date, right? Like I haven’t been on a date yet, and we all went and met her, and I told her , like, the bot, and it’s become a joke since then, like-

Laurie Segall: Wait, no, don’t stop there. What did she say? So you go on the date…

Shane Mac: Yeah.

Laurie Segall: …were you like, that was a bot?

Shane Mac: I was like, let me show you something. I was like, you’re probably going to hate me, uh, but I want to show you that the bot actually is the one who sent the message that you responded to and, she thought it, she thought it was, uh, funny and she also likes technology, she worked at Google, and uh, so she was open to, like, techy type stuff, and like where the future was going. Then it just became a joke, we were kind of just joking about it, and I was like, I just wanted to save time so I built this little keyboard.

Laurie Segall: So she was like open to it?

Shane Mac: Yeah, I’ve been in a situation where she wasn’t.

Laurie Segall: Let’s talk about that.

Shane Mac: Uh, I won’t say her name.

Laurie Segall: Okay.

Shane Mac: But we went on a, we went on a date on a Friday night, not ’cause of the app, but she worked at a dating company that is probably one of the top three.

Laurie Segall: Uh-oh.

Shane Mac: And she spent a lot of her time making it very personal, better responses.

Laurie Segall: Mm-hmm (affirmative).

Shane Mac: So that things like this, like weren’t- it wasn’t about the swipe anymore, so you can probably guess what dating app it was.

Laurie Segall: Yep.

Shane Mac: And the next night I was like, “I’ve been thinking about the dating space as well.” And I showed her using one of the platforms the keyboard. And it- she literally was insanely offended. She was like, this is- “If you give this to people that aren’t their words, could you have everyone in the world manipulating everyone?”

Laurie Segall: Right.

Shane Mac: And I was like, “That’s a fair question.” And I said, “But how do we learn in general?” Like, my thing is that if I can teach people to be more empathetic and the language is better you’re just reading in a book anyways. Like, all your brain is, is like whatever you’ve read. So, all you do in life is read, remember, and repeat. Okay. If I can put a keyboard at the moment of time when you have to think, I can actually help people.

Shane Mac: And I think there’s a much bigger vision with this that is giving you responses and suggestions at the time of the right conversation and context way beyond dating. But also to make people better, ’cause I watched some of the responses that guys send on dating apps and they’re totally dicks. Or they’re just rude or they don’t- they’re like, and I think you can help that. You could actually be suggest- so, she got offended, she actually I literally think she was like, “I’m gonna leave the date.” then we went to a party together and she left like an hour later ’cause she was just like, really- it like, it was a, like a- a totally offensive to her.

Laurie Segall: Wow.

Shane Mac: I was like, holy shit. I called Stefan I was like, it’s either the greatest idea or the worst idea because like, shit like that is so visceral. It’s like, okay it’s either gonna blow- it’s like, Snapchat early on becomes a thing because it’s all about the like shit like that is so visceral- Snapchat early on becomes a thing because it’s all about like

Laurie Segall: Sure.

Shane Mac: Nude pictures, right? I’m like, okay is that like the bad PR stories gonna make the thing actually work? ‘Cause everyone I gave it to fucking loves it.

We need to take a quick break and then we’ll be right back.

Laurie Segall: So I was thinking about this ’cause I’ve been on the dating apps for a little bit on and off, and you know, you talk to people they’re like, “Ugh, I’m off the apps, I’m on the apps, I’m off the apps.”

Shane Mac: Yeah.

Laurie Segall: Because it’s a real problem.

Shane Mac: It’s literally like a pendulum of emotion.

Laurie Segall: And I joke that like, I think I’m like a relatively nice person, and I think like I become a bit of a bot on the dating apps because like, I am sorry if you’ve had to deal with me on the dating apps because like I just don’t feel like I have the capacity to respond in- you know? And not to be like, make you a confessional but like, it’s really hard to, um, to like respond to people and like, with as much you know, it’s just like a lot. 

Shane Mac: Everyone says this, though.

Laurie Segall: You know when there’s so many people, or there’s so much, or they’re just like, and you don’t have that emotional connection to folks. I very much wanted to judge you for this. Now like, we were swiping and now we’re literally creating a bot to do it for us. Like, oh my god.

Laurie Segall: But I actually think, um, there’s a lot of nuance here because something you’re talking about is, it’s a reaction to something that I think a lot of people are dealing with when it comes to, to the friction of this moment. LIke I think we’re all in this weird moment with dating in the apps and people like, finding people and like, this problem. I think there’s a real problem with it. Um, so you’re kinda on to something, but I do think it could go both ways. 

Laurie Segall: could we read like some of your, your messages?

Shane Mac: Sure.

Laurie Segall: ‘Cause I feel like people are like, what does this even mean? We’re like talking, like very above it. I want to- I want people to actually have an idea of it.

Shane Mac: So, the first thing that, uh, I think we did is we designed it for Hinge.

Shane Mac: What’s fascinating about this is because it’s a keyboard it works on every dating app.

Laurie Segall: Hm.

Shane Mac: And you can’t stop it because it’s built into the keyboard.

Laurie Segall: And explain that to folks, so it’s like literally-

Shane Mac: When you install it, it’s, it’s uh, a different keyboard. So, right now your keyboard is full of letters. You- every, like this is how I view the world. I’m like, we’re all sitting on our phones manically typing letters with our thumbs, staring at our phones trying to make words, trying to make sentences so we can make meaning. And I’m like, this is gonna reverse. Like, it’s- it’s like, frying our brains I think. Like, it’s gonna go to intent. My intent is I really want to go on a date with Laurie, what’s the best thing to say to Laurie? I don’t know, based on everything I’ve said in the past, the software should be able to figure that out.

Laurie Segall: (laughs) I mean you’ve been texting me since 2012 and there’s probably you know some data in there Shane. 

Shane Mac: Let’s put it in the bot. And so, there’s a photo of Jessica on a hike.

Laurie Segall: Okay, so for- we should describe to our folks, like yeah so folks who are just listening and can’t see. There’s Jessica, and there’s a pretty waterfall and is Jessica doing a ballet move? Is that a ballet move?

Shane Mac: Yeah, that’s a yoga warrior pose I believe.

Laurie Segall: Okay, see this is Laurie doesn’t do yoga. Okay.

Shane Mac: (laughs) And then the first thing the bot then responds, so the keyboard then turns into intents, not letters. So, now you have the categories and stuff, and it- it recommends the hike category.

Laurie Segall: Okay.

Shane Mac: ‘Cause she’s on a hike in the woods.

Laurie Segall: And what does the, and so what does that thing that- and so, now ’cause people can’t see it, it just auto populated some-

Shane Mac: It basically writes the sentence for you. It doesn’t hit send automatically.

Laurie Segall: Okay.

Shane Mac: So that is controlled by the dating app.

Laurie Segall: Okay.

Shane Mac: So- but it can write all the responses automatically based on an opening line, based on, it’s a photo of a hike so it says, “Where was that beautiful photo taken? It looks beautiful, and I love going on hikes.” Uh, and I just hit done and then hit send. And …

Laurie Segall: Oh, wow. Okay, who’s this?

Shane Mac: You know, to go here, do a little curious line. What’s the best taste of food you’ve ever tasted in your life? Can we go there if we make this thing work past 17 and a half dates?

Laurie Segall: Okay, wait but can we tell people who we’re- now we’re talking to a girl named- what’s her name?

Shane Mac: Alyssa.

Laurie Segall: Alyssa. She looks so nice. Uh, see I feel so bad that you’re just like, but so- this is where I feel so conflicted. It’s just like, you’re like auto populating like things into another- that’s still Alyssa?

Shane Mac: But do you ever ask- you know what I actually- so the way I justified it with myself was two ways. One, I watch everyone use the dating apps and they always let their friends talk for them.

Laurie Segall: Hm.

Shane Mac: So why can’t your friend be a bot? Why can’t the person helping you date be a bot? The second one is, I don’t think the future is this- this endless, um, connection. Like the apps have now commoditized connection. There’s two- everyone’s connected in the world. Cool. So, now everything’s a dating app. Facebook, Instagram, it’s all just connections of people. So, I think the future is back to match making. But why do I have to hire a person to be a match maker?

Laurie Segall: Right.

Shane Mac: When software can be so much better at match making than hiring some person to like, call people randomly or search online? Like, my bot can go find the person, research the person, let our conversations talk based on past data and be way more efficient at match making. And I think it’s gonna, the pendulum’s gonna shift because right now everyone’s like, stressed. This endless inbox, it’s happening.

Laurie Segall: Sure.

Shane Mac: You have all these connections. I think it’s gonna go back and you’re not gonna want it. You’re gonna find me three dates for this month that are amazing.

Laurie Segall: You know, I think what the issue is, and I think we can come, we can circle back to this is, is honesty though, right?

Shane Mac: Totally.

Laurie Segall: and i think but i htink what you’re doing is interseting but the problematic part and what you’re struggling with too is like-

Shane Mac: Disclosure.

Laurie Segall: Disclosure.

Shane Mac: Totally.

Laurie Segall: and the whole issue of tech and why we are where we are right now is like the lack of transparency Like, what are we getting and who are we talking to? And so i htink like that’s like at the heart of this. Which is like what’s authentic anymore? And as technology becomes more human do we have the right to know? And should we?

Shane Mac: Or do we even know what is really-

Laurie Segall: Right.

Shane Mac: Our thoughts or what is the computer’s? Like, you use Gmail-

Laurie Segall: And-

Shane Mac: It responds for you.

Laurie Segall: And does it matter?

Laurie Segall: like, and maybe that’s the thing as you build this should be something you’re thinking about, right? Like-

Shane Mac: Totally. Disclosure is huge. And you saw google launch google duplex, right? And it could call sounding like John Legend, and do things for you.

Laurie Segall: Right.

Shane Mac: And they came out the next day and they said, “It’ll always disclose when it’s a bot. This is an automated assistant for Laurie Segall, I’m calling to make an appointment.” And disclosure I think is a massive one.

Laurie Segall: And so, the issue right now is that it doesn’t.

Shane Mac: Yeah, but it’s interesting when you think of that, like if they’re my lines that have gotten better and it’s helping me communicate, and I can actually edit it after I tap the button and then hit send. Is it my words, or is it the bots?

Laurie Segall: I don’t know.

Shane Mac: yeah. Who- if, if it’s suggesting something to me-

Laurie Segall: I guess you’re right. So if it’s your words, like do you have to be like, well they were automated? I don’t know.

Shane Mac: If I copied it off the internet because I found it and I wanted to use it and edited a few words of it to make it my own is it an automated response or not?

Laurie Segall: I mean, I guess would the other person feel violated? if I found out that we matched on a dating app here’s where it would bother me.you know, if you had asked me a question that, uh, that required some vulnerability from me-

Shane Mac: Sure.

Laurie Segall: If I, took a minute to respond, like something- okay, there was, there’s something on the keyboard that’s like, “Tell me something on this silly dating app- tell me something about yourself that this silly dating app wouldn’t reveal about you.” 

Shane Mac: (laughs)

Laurie Segall: Just if you’ve ever encountered me on a dating app, I would never say that but if I actually took a minute and I like, had this like real answer, and I was like, “Well, you know, I really um, growing up I was really insecure about X, Y, and Z.” And I like, took a minute to come out and tell you that, and then I realized later that that was like, something automated that you sent to me, I think I would hate you. I mean, I think I’d be really pissed off about it. And so, then you get a visceral reaction, and this is me as like a tech reporter of many, many years who can understand both sides. So-

Shane Mac: Totally.

Laurie Segall: Um, you know, so I think when you, when the machine even if it is kind of pre programed gets some kind of vulnerability out of you, it feels like you’ve been violated in some way. So, like I mean, by the way this is like such like a weird conversation to be having, but I think you kind of have to have it ’cause it’s such a human conversation and it is totally the future. I don’t care if people think this is crazy, like I don’t think-

Shane Mac: Totally.

Laurie Segall: This is that crazy. ’cause you were nervous to do this interview, right? Earlier-

Shane Mac: For sure, I’m still nervous to do this interview. There’s a reason we haven’t put it out in the world, and it’s I- I truly believe that language and automated language has insane benefits to the world in the future. Like, that’s why I like working on this space. I think everyone’s gonna be able to learn from their Alexa and their Goggle Assistant, and do things with it and their own bots. And it’s gonna be much easier than the internet. But there are areas where I worry it could be misused. I think about a guy that might not be a good human getting access to a way to be more vulnerable, ask better questions and get someone to respond. And then completely going on a date that is not, and the, the lady going and it is completely not who she thought it was gonna be.

Laurie Segall: Yes.

Shane Mac: And that sounds like that could be, you know, risky. But then I’m- then the other side of that is like, if it’s teaching people to communicate better how do we learn? It’s just language that’s teaching people what to say. Like, how would they know what to say in the first place?

Laurie Segall: Well, so the unintended consequence of this is-

Shane Mac: Yeah.

Laurie Segall: Beyond kind of the disclosure of it, and people kind of feeling violated is it could be used by people to just kind of like, be sociopathic, like in some kind of capacity.

Shane Mac: Totally. For sure.

Laurie Segall: And like, you already have people, um, I would say using the dating apps in ways that like, are dehumanizing kind of like-

Shane Mac: 100%.

Laurie Segall: You know, so it could almost make them like go on like a turbo rampage, or something, I don’t know-

Shane Mac: For sure.

Shane Mac: That’s why I got nervous and it’s the reason that, it was just an experiment, and we were really interested in how to create, I mean I think the like, leadership keyboards or anything. Like, I want to know what, I told you this, I want to know what Dale Carnegie would say when I’m reading an exec team email. And you kind of want to respond you know, you’re kind of mad and you’re like, you have a moment of like, I’m gonna respond to this email. Like, I would love to pull up the keyboard that’s like, the leadership keyboard that is reading their email and is like, hey here’s a way to ask questions. Here’s a way not to like, and suggest what I should say. And I think that is the future. It’s already happening. Like, google is, literally every time I hit tab in my Gmail like, it writes for me.

Laurie Segall: I was talking about this with a friend of mine, um, who uh, has some issues with, um, a father-in-law of some sort, you know, and they were like, get stressed out every time uh, they message. And they’re like, I wish I had keyboard to just handle those, you know, those interactions, right?

Shane Mac: Totally.

Laurie Segall: Um-

Shane Mac: I mean, it’s like the Zack Brown song, like, when I couldn’t find the words to say.

Laurie Segall: Mm-hmm (affirmative).

Shane Mac: And I feel like that’s so many times in life for so many people. And it’s just a, a way to suggest you know, what to say in the right context and teach people what they should say to be a better human. But if you train it with the wrong models that are negative connotation or bad language-

Laurie Segall: Sure.

Shane Mac: Then you could teach people to be worse humans.

Laurie Segall: It’s like a Fine line, like you gotta be careful what you wish for because you could have the unintended consequence of like, making people even less human.

Shane Mac: You can pick up a book right now that’s a terrible book and read it and change your brain to think that that’s true and-

Laurie Segall: Right.

Shane Mac: Become a, a-

Laurie Segall: Although, technology always kind of goes viral in ways that books, you know-

Shane Mac: That’s why I actually, I watched you know, I probably gave it to like 30 people.

Laurie Segall: Mm-hmm (affirmative).

Shane Mac: And I haven’t seen technology since like, even like Twitter, like I remember the first time I tweeted in like, 07 and it was a moment of like, holy shit I can text anyone in the world. And I remember that feeling you’re like, wow, this could be something. And I had that feeling with this, ’cause I was like everyone I gave it to is like, this, like they have an emotional reaction to it. Positive or negative. And they love it.

Shane Mac: And I’m like, oh, if I put this out in the world, like it could they- it’s probably a good company because I actually believe suggesting words to people to get better responses is a much better business model than swipes. 100%. So, then I’m like, the dating app business models are broken, I’ll just build this as a company. But I- I don’t know. I’m literally just sitting conflicted

Laurie Segall: Who have you given it to? Anyone good? Anyone we know?

Shane Mac: I won’t, I- it’s, because it’s controversial and I’m putting myself out there I won’t put anyone else out there.

Laurie Segall: Okay, but what- what has been kind of their reaction?

Shane Mac: This works effing amazing, let’s keep building more of it. And I haven’t worked on it in a year. Like, we built it, we put it out privately.

Laurie Segall: Mm-hmm (affirmative).

Shane Mac: It’s been on my phone for a year, it’s the most efficient thing I’ve built in a long time.

Laurie Segall: Oh my god.

Shane Mac: And everyone that uses it loves it, and they’re always just asking to do more. And I’m like, this isn’t a company. Like, I have a job- like, I don’t have a company-

Laurie Segall: This has been like your side gig.

Shane Mac: It was just a fun thing ’cause we were building bots and I was like, I want to see what it’s like on the consumer side.

Laurie Segall: Sure.

Shane Mac: And not- there is a company to be built there, I don’t know if I’m the right person to do it, put my name on it. So.

Laurie Segall: Oh, well now-

Shane Mac: You should do it.

Laurie Segall: We now put this out into the wild, yeah. Um, I don’t know if I- I, look, I think ethically, I think ethically uh, it’s really in the gray area, but I understand the problem that you’re talking about, but I think that there are also like, you know, people could really misuse it

Laurie Segall: so I want to talk about, uh, I tried it, um-

Shane Mac: I want to hear this.

Laurie Segall: And so, and so um, I just like, okay. So, you first told me, like you told me about keyboard, and I know I’m having trouble making eye contact with you 

Laurie Segall: So as part of this, 

Laurie Segall: you were gonna help me create a keyboard. And so, you were like, “Well, we don’t really have it for a woman.” and, and so you were like, “What would you say to people on the dating apps?” And so, I had a lot of trouble,  my co-founder and I Derek, we were, he was sitting with me while we were trying to create prompts. I was like, looking up through the dating app and think of things to say to people and responses. And- hands down, like, like-

Shane Mac: (laughs)

Laurie Segall: I literally if you, if you had heard this con- actually I think we- we did record it. So, if you listen to it you might think I might die alone listening to my responses. Um, they were awful, because it’s like hard to anticipate what I should make my bot say, 

LS: So lame, like no one’s going to respond

DD: I like your vibes and i like your ehtos

LS: i like your ehtos

DD: you don’t say stuff like “you have nice eyes”

LS: that’s creepy

LS: (laughs) what else?

DD: well let’s say your pickup lines, if you like somebody you’re more likely gonna like criticize them than say something nice. 

LS: yeah cause i’m like a 10 year old in the making. Um, let’s see. There’s a lot of- and so- it should be like the keyboard picks up if it’s like a hiking picture. So maybe say like “ you look very athletic kind of?” i don’t (laughs)

DD: (laughs) wait this is really explaining a lot to me so 

LS: why i’m single?

DD: I’ve known you for 10 years and like why like why do you have so many male problems? Cause you just like don’t know how to speak to them i think.

LS: definitely not on these apps.

LS: Derek adn I had this whole session where we were trying to create like these prompts where we could auto populate into my keyboard. And that was interestin nonetheless.

Laurie Segall: So then we sent some of them to you- I mean, they were like (laughs) what did I say? Like, I like your ethos?

Shane Mac: Yeah.

Laurie Segall: By the way, I would never say that to a human being.

Shane Mac: I have them in my phone.

Laurie Segall: i mean like Please don’t, you know. Um-

Shane Mac: I can use your responses and see if they work for me.

Laurie Segall: I mean, they probably won’t. I mean, I like your ethos, if you say I like your ethos to that woman she would-

Shane Mac: Do you have a dog?

Laurie Segall: She will not respond.

Shane Mac: Here, let’s send it, I like your ethos.

Laurie Segall: Well, a lot of people have dog photos. So, like yeah. So, by the way to our listeners he just wrote I like your e- his bot just wrote I like your ethos to a woman on Hinge, um, and that was based off of my keyboard-

Shane Mac: (laughs)

Laurie Segall: So, I now have the keyboard.

Shane Mac: We call it words.

Laurie Segall: Words. I have it, uh, installed. And I used it on, um, just ’cause I was like, I want to try this and see how I would feel about it.

Laurie Segall: First of all, we didn’t use all my responses. I used some of yours because I apparently didn’t make a good enough one that like, it could carry a whole conversation. but I, so I went on Hinge

Laurie Segall: So, it’s a bot, right? This is the right way to say it, like it’s a bot.

Shane Mac: Yeah. anything that can write for you and have conversations.

Laurie Segall: Yeah.

Shane Mac: The limitations of, of this bot is that, you know, we didn’t have a big data set ’cause it was just you to try it. But it still works. Uh, so it can’t optimize yet, but it would over time. Uh, but it also, Hinge in the apps, you know, they’re not allowing you to send a message automatically so you still have to hit send.

Laurie Segall: Right. Right.

Shane Mac: So, that’s the- that’s the reason it can’t just be fully conversational.

Laurie Segall: It’s not fully, like this isn’t the smartest version of it, this is like a very, like, new, new ver- you know, this isn’t something that’s super technical.

Shane Mac: Totally. And it could be fully conversational, but it wouldn’t work on the dating apps because they don’t allow you to like, unleash the bots and just have like a full inbox conversation.

Laurie Segall: Right. Um, so god, I mean should I change his name because, well he was not happy. Let’s just call him Adam, I’m gonna change his name because he was not-

Shane Mac: You told him?

Laurie Segall: This is what I’m gonna, so- I know. You’re- I know. Here we go.

Shane Mac: (laughs)

Laurie Segall: So, um, my bot said- these are all the pre programed answers, and I, I challenged myself. I didn’t want to come in as the human. I wanted the bot, I wanted only pre programed questions or answers to this. So, my bot said, “I like your ethos,” I’m reading the message now. I screenshotted it ’cause I was sending it to you. It said, “I like your ethos.” That was pre programed.

Laurie Segall: And immediately he wrote back, “I can see why.” Like, recognizes. And then, I mean, by the way, we’ve gotta make this bot better because I would never say this, Shane. It says, “I mean, if I said I love Taylor Swift, would you hold it against me?” And then he said, “Of course not, it would simply fit.” I’m just like, dying at this point. I’m like, I feel so- I feel like such a jerk.

Shane Mac: (laughs)

Laurie Segall: So, then but I kept going 

Laurie Segall: I said, “Tell me something I wouldn’t expect about you. Dot, dot, dot. That I wouldn’t get from some silly photo or dating app.” he said, “I spend a lot of,” and he said, “I spend a lot of time thinking about my words and behavior, which doesn’t always amount to doing the right things. But I guess you already ascertained that from this silly dating app.” So, things were going there. And then I didn’t really know what to say, so I just went for the bot. And I said, “Should we try IRL?” Which is pre programed into the bot under, what is it under? It’s under-

Shane Mac: Connect.

Laurie Segall: Connect, under connect. (laughs)

Shane Mac: Get off the app.

Laurie Segall: And then he’s like, “What’s that? Betrayed by my age, good lord.” And then I guess he looked it up and he said, “We should.” And then I went- I, I just pre programed another answer that said, “Can we just skip this endless banter on this app and go do dinner some night that works for you? We can meet for a drink before so you can bail if I’m the worst.” By the way, these are all your keyboard answers, these are not really mine, right?

Shane Mac: This is a community too, it’s not all mine.

Laurie Segall: Right, these are all the, the answers. And he said-

Shane Mac: It’s optimizing like, putting two different things together, right?

Laurie Segall: Right.

Shane Mac: So, there’s the, that one is some kind of language around like, getting off the app.

Laurie Segall: Yeah.

Shane Mac: ‘Cause that usually is a thing.

Laurie Segall: Yeah.

Shane Mac: And also, everyone is nervous to meet people that like-

Laurie Segall: Totally.

Shane Mac: Don’t look like their photos.

Laurie Segall: Right. Um, well, we never had the chance to meet. Let me tell you why, Shane. Um, I said- then he said, “Let’s just meet for a drink, that’s more my speed even though I don’t drink, a bar lounge is fine.” And then I didn’t know how to end it, so I ended again with, “I like your ethos.” And he wrote, “Very good, then.” So, my bot had set up the date, right? And so, then I mean, by the way, I didn’t say one thing- I mean, that was all based on keyboard. I was like, in shock that that even worked.

Laurie Segall: I mean, and also like, I was like wow, the, I mean, Who would want to go on a date with that person that just, you know, like I hated every per- like, I wouldn’t want to date me after that. But, um, I uh (laughs) so then after, I just- after a couple minutes, 

Laurie Segall: I was like, you know what, I feel kinda bad. I felt really conflicted about it. You know, I’ve covered ethics and technology my whole career, Shane. So, I decided right then and there, not in person to disclose. And I was like, you know, and- and I wish I had these conversations, but I don’t for what I’m about to say. I was like, hey, you know, I just want to let you know, I was like “Can I be honest about something?”

Laurie Segall: And he was like, “yeah.” And I was like, “I just want to let you know that, um, that this was like, pre- those were pre programed answers. Like, I’m working on this thing.” And you know, and those were- those answers were pre- that was like, actually like a bot. But like, “you know, I also um, would love to meet, and I know it’s this weird thing. I cover tech, and you know, I’m trying out this thing. But you know, you seem like an awesome person, and I know that was so weird.” And you know, I thought that was, I thought that was-

Shane Mac: Where did you say this? On Hinge?

Laurie Segall: Yeah. All hell broke loose. Like, what did I call him, Adam? I changed his name for security purposes.

Shane Mac: Yeah.

Laurie Segall: Um, Adam went crazy. Stage nutty. Adam was like, you are crazy, you’re psychotic, like you’re disingenuous. Like, I think you’re like the worst person ever, like I don’t even know what to believe. Like, who do you think you are? And I was like, oh, god.

Laurie Segall: And I was like, oh my god ’cause I probably just gave this guy like a trust. I probably gave him trust issues. I gave him his worst dating experience ever. I’m someone’s bad story, which I’m sure I have been in the past. But like-

Shane Mac: (laughs)

Laurie Segall: Now for a whole new reason, tech related at least, so I’m on brand. But like, oh I felt so bad. And it was like, it was like this whole thing. And um, and I mean, he was really aggressively angry at me. And then, so I went to go try to apologize and then he had blocked me. So, I’m blocked on Hinge by this guy, so that was crazy. And it was such like a visceral emotional reaction. And so then-

Shane Mac: Should you have disclosed or not?

Laurie Segall: Um, you know, I’m happy that I- well I don’t know, I feel really conflicted about it. So, now it’s like, should I have just met with him and seen if we had a connection and then told him? But then that’s like, the root of the issue like, is there something wrong with it? Like, that you have to disclose it? Like, you know, do you know what I’m saying? Like-

Shane Mac: Totally.

Laurie Segall: You know, and I think there’s so- (laughs) I’m so conflicted, like you know, and I felt bad about it.  but I understand what you’re talking about when you say like, there’s a problem with like, you know, with the language as we have it, right? And, and so I was also on, I’ll- I’ll go with one more. I mean, because this thing really does work very quickly. this is on Raya, which is another dating app for our listeners. Um, this one’s like, some guy I just don’t respond to anyone. I just- I find it exhausting.

Shane Mac: Hence, the point.

Laurie Segall: Exactly. And this guy said, “Hey, what’s up?” I just didn’t respond, and then he was like “Pizza or cupcakes?” Like, I’m not gonna respond to that.

Shane Mac: He’s a bot. (laughs)

Laurie Segall: And so, my bot responded, I decided I was like, this is the perfect way for my bot to respond. And I said can we- this is the pre programed response of keyboard. I said, “Can we just skip this endless banter on this app and go to dinner some night that works for you? We can meet for a drink before so you can bail if I’m the worst.” This is the pre programed thing, I just pressed a button. Next thing you know, “I respect the directness, I’m around next week. That work for you?” Like, this happened in two seconds. And by the way I just  didn’t respond because I was too busy like, shaking over like what happened with Adam and how upset he was.

Laurie Segall: Um, so I- I think you’re really on to something really weird and interesting. Um, and- and by the way, another one too, like so this thing really does work, um, you know, I do worry, um, you know, will it impact trust? will we now all have like, massive trust issues too? I don’t know. Like, what do you think?

Shane Mac: I think we are gonna have a robot that is helping us speak in many different ways, whether it’s grammarly on top of your browser, whether it’s a keyboard that’s adjusting answers, whether it’s Gmail completing your sentences for you, it’s happening everywhere. Um, I think it’s really more important to focus on what are the models in which we’re building the technology so that they’re optimized for empathy, they’re optimized for good, and if it’s already happening- I look at the world in two ways.

Shane Mac: If something’s inevitable, do I want to learn most about it so I can be helpful in that space? Or do I want to ignore it? And I’ve always in my career, in my life chosen to, to do that. Like, the biggest argument with our company is like, are you putting the call center people out of jobs? And I’m like, or we have to retrain all the jobs. If it’s gonna happen inevitably, why not spend our time saying how do you train bots? How do you train language? What are gonna be the opportunities it creates versus what- or what it you know, can kill? Uh, and that’s how I just view the world. And I view this the same way. There’s something happening here. I don’t completely understand it myself, like-

Laurie Segall: Sure.

Shane Mac: The emotion of what it’s doing on the dating apps. But there’s obviously a huge problem because everyone that uses it loves it, but is very conflicted by it. Um, and so I’m like, that’s why I didn’t put it out there, I’m kind of sitting there watching it and I’m like, okay. And that’s just the version one. 

Shane Mac: We haven’t even like, we haven’t, just, this was just like a random experiment. Like if I would have innovated on that for a year, the whole thing would be talking for you. IT’d be like crazy responses that are getting better, and like, uh, I don’t know. I don’t think dating apps look like what we see today. I don’t think Hinge, Bumble, Raya, all these things that just like endless connection of faces. The swipe is like walking up to someone at a bar, all right?

Laurie Segall: Yeah.

Shane Mac: And now it’s gonna go to the language. It’s more about important about the words you use than it is about what you look like. Cause there’s endless connection on the thing. Its and now I’m like, looking at it of what does the next phase look like, and I think it, if both sides have the bot, it changes the dynamic.

Laurie Segall: Mm-hmm (affirmative)

Shane Mac: When one side has the bot, it’s not fair. And if it’s not disclosed then its not fair and also it feels manipulative.

Laurie Segall: Right.

Shane Mac: But when both sides have it and you’re aware of it, I think everything changes.

Laurie Segall: And. And maybe, I mean this idea that in the future our like, uh, I think the Hinge founders talked about this a little bit. Like we make all these massive decisions in our lives like based on data. Um, you know but, when it comes to love we go with like, our gut, right?

Laurie Segall: Um, and and now I I think a lot of these companies are trying to figure out data driven ways to match us better, and so I think, you know there’s nothing more interesting than AI, and bots and the future and how they can connect us in a way um that might based, that might be more personalized based on our data, and I, I think there’s, there’s certainly something there.

Shane Mac: I mean, today, even the way we choose someone is so visual, right?

Laurie Segall: Yeah.

Shane Mac: And then after one minute of meeting someone, and you think they’re cute, the rest of your life is talking. And so why not optimize for the latter? Why not figure out if you’re more compatible based on our conversations, rather than what you look like?

Laurie Segall: How does technology, you’re a technologist so how does this, how does technology do that?

Shane Mac: Because if it can watch your conversations, it can know both your emotion, there’s a cool company, um, this, I was with the lady last night Eva and she has a company called Mia. Um, and they can analyze your conversations and they can know if you’re interested in the other person by the way you’re speaking. So they’re actually sitting on top of WhatsApp, looking at your conversation and saying “That person is interested in you.” So, I think in the future, that is definitely going to be how this plays out. And if it can watch the people I’m interested in and how I speak to them, then it can definitely design a conversation model or ways to respond that are  me, to language that I also like from the other side. Um, you know the Hinge founder, it’s funny, like, his motto is “Delete the App.” Then why do I have to install it?

Laurie Segall: Hmm.

Shane Mac: Like, I don’t think the future’s installing an app at all. And that is where I think it’s going to change.

Laurie Segall: What, so what does the future look like? You talk about bots, you talk about, like having these bots that date for us. Like, what, what is that, like..

Shane Mac: Hey Laurie, who do you like, you know, what type of, uh, guy do you like to go on a date with, uh, height wise?

Laurie Segall: I mean like, I’d say like, you know tall-ish?

Shane Mac: Fancy dinners or dive bar?

Laurie Segall: I mean like, more dive bar.

Shane Mac: Great.

Laurie Segall: With like, the idea that like, fancy dinner we could do every once and a while, but like lets not do it all the time.

Shane Mac: That, that will be the bot of the future. And it’ll just keep talking to you and then that will be, it’ll go find that type of person. And the other, um, you won’t have to install anything. It’ll happen within your text message, and just like a friend texting you; “Hey you should go on a date with this person” it’ll be an automated bot saying “Date’s tomorrow night at 7 o’ clock. I have a date for you. You wanted 3 dates this month. Perfect.”

Laurie Segall: So why do you think you haven’t found someone?

Shane Mac: Do you want a longer conversation?

Laurie Segall: No, I mean like, this is the

Shane Mac: I got out of about a 4 year relationship, uh,

Laurie Segall: Yeah.

Shane Mac: A few years ago.

Laurie Segall: Okay.

Shane Mac: And… then I just kind of buried myself in the company.Uh, and, you know, since April we just got acquired. So, I’m, first off I was more stressed than I’d even been. Running the company and just, I almost, like, was so stressed running it that I was like, not interested in dating or anything serious. I think the insecurity in myself is like, I always thought like, what if the company fails? And I didn’t really want to date someone and then be like, uh, I’m, I don’t know if this is gonna work. And I had like this insecurity that I dealt with now in the last few months of like, being post this acquisition. I was like stressed out as hell, I was kinda ig-ignoring the dating life.

Laurie Segall: You were worried that if  the company failed that you would be a failure, that

Shane Mac: Yeah, it was like, a very personal thing. And I think I was pushing people away. And not letting anyone get close as I was going through running the company for, you know. 6 years. Uh, and I’ve kind of gotten over that now. 

Laurie Segall: Well I think building a company and, um, and a lot of people don’t talk about this, we’ve both been in tech for a very very long time, I think it’s actually really really hard,  it’s a lot harder than it looks, um to build a company, to have a company acquired, um, to withstand the pressure of it, to have, you know, all, all of that. It all makes sense in the rear view mirror. And even in the media we can talk about; “and then they sold it for x amount of money.” Like no one talks about the moments, that are terrible. Which a lot of the times, when people are telling you you’re gonna fail and you have a thousand decisions to make and you’re not sure any of them are correct and

Shane Mac: Yeah.

Laurie Segall: you know, and you’re scared to disappoint anyone including yourself, so I can imagine, that is uh

Shane Mac: You’re out of money in 30 days. But then you have to raise around, you get like three different M&A offers, one of them falls through and like for a year and half you’re going through this crazy spiral. 

Shane Mac: Like I would almost use dating, actually go on dates as a distraction. But nothing I wanted to like, get committed to. Cause I was had my own deep, like, insecurity I think that I thought it was you know, I didn’t know, I didn’t know what, if I was going to make it out of the thing.

Laurie Segall: It was like a numbing.

Shane Mac: Yeah.It was, it was very, uh, just try, like when I was so stressed, I, I learned a lot by myself of like, I didn’t even want to spend time with my close friends when it was really hard. When like I was really like oh shit. Like, you know, we gotta pull this through, and we gotta make some things happen or this is going to implode. Um, I learned a lot of, I didn’t want to hang out with anyone close to me because they would always ask me like, how’s work going? What’s up with this? And I was like oh my God.

Laurie Segall: Yeah.

Shane Mac: Like, I don’t want to talk about it. And so dating actually, (laugh) was a way to not have to talk about that kind of stuff. Um, so I like, pushed away the hard stuff. Which I learned a lot about later and, but, the last 6 months of it, a very personal discovery. Trying to get healthy again and, you know, I gained 45 lbs running the company. So like, hiring a trainer, getting back in shape, mental health, hydrotherapist, all the shit. (laugh) I basically like, and from May I was like “listen, I need to like, be more thoughtful and, uh, about myself. And just try to make myself better”

Laurie Segall: What do you think are the biggest changes that you made now that you’ve kind of, you know, you’re kind of coming out of it now, what do you think are the biggest changes you made now?

Shane Mac: Um. A few things, I would say the first area is, you know, I moved somewhere that wasn’t in tech. I live in Nashville Tennessee. And, uh, it’s way calmer. People, people, a lot of people, um, work there to live, not live to work. And I think for the last 12, 13 years I’ve just, like I was in SF, I was downtown, I just worked. Uh, and it’s a lot more like family oriented. So I kind of think like, wherever you’re around, changes your perspective and so that’s been really good.

Shane Mac: Being open to like going to therapy and stuff has been amazing. Uh, learning so much about like why, what I push away and why I ignore things and why, uh, you know, did I become less of a good close friend during all the stressful times and all that kind of shit.

Shane Mac: So it’s been an interesting kind of last, 6 months?

Laurie Segall: Um, in the last 6 months you know I left my job at CNN

Shane Mac: Yeah.

Laurie Segall: And one of the biggest things I wanted to talk about with this, this media company that we’re launching is like mental health, right?

Shane Mac: Totally.

Laurie Segall: I very much covered technology I think from the second wave beginning in 2009/ 2010 watching , I mean we probably met around that time

Shane Mac: Delusional optimism, is how it felt.

Laurie Segall: Yeah, like, I was so optimistic about it. but, but I think I watched a, you know, my earliest interviews were the creators of um, Instagram and Uber, you know and watch these tech companies. Watch the minnows become the sharks and watch them disrupt culture and, in these extraordinary ways for good and for bad. Um, and I think, you know, watching like the mental health stuff like and how this impacts everyone, including myself, 

Laurie Segall: You know I think it’s actually really important. Because I’ve always been one of those people that believes that tech is coming, and like, we gotta talk about it. And I believe, like, as weird and fringe as this may seem, that reaction that you get when people use keyboard, and like the reaction I got when I used it for the first time is disruptive.

Laurie Segall: It means its coming down the pipeline so we have to have these ethical conversations and mental health is a big part of all of this stuff too. and bots in the future, I, I can imagine this keyboard and this thing that you’re building, could actually be really interesting for mental health and AI and bots could actually be something, um, for people who are struggling with mental health issues. 

Shane Mac: If you can watch everyone’s language, you can know how everyone feels.

Shane Mac: You can know if they’re anxious, you can know if they’re depressed. You can just do it just by analyzing the words they say. And so that, from a, like a, um, preemptive mechanism? For mental health, that’s where I get like super excited. There’s so many, um, great things that are coming with the ability to analyze language and provide suggestions or get people help. Uh, just based on the words they use.

Laurie Segall: Like what? Like, what do you mean by that?

Shane Mac: If I’m having a conversation with you, you can know based on the technology, whether or not, like I’m speaking in a depressed tone versus yesterday.

Laurie Segall: Sure.

Shane Mac: Uh, and that’s amazing. To make that aware to you. Like, you know, like, going through the company there’s times I definitely was depressed as hell. And you don’t really, it’s weird when you’re in it. Its hard to, you, you just kinda, like, uh I don’t feel like I wanna do anything. It’s hard to like get up and motivate yourself, it’s hard to reach out to friends. Uh, its’ like having something that isn’t biased, that’s software that can help you and guide you and you know, you don’t even know where to turn and look. I think that can be a very powerful thing.

Laurie Segall: Having something say “you’re depressed right now. This is what you can do.”

Shane Mac: This is what you can do. Here’s how I can help you. Uh, and it knows, ’cause you’re still doing, people are so addicted to their devices right? That’s a whole nother problem. Its the whole thing I did in the last 6 months was getting off my device, I mean our mission of our company was to build software to get people off of using software. And I still believe in that mission. I think the phone is getting fragmented from a phone device to a bunch of little devices like the watch and the airpods and the i’s and all that stuff.

Shane Mac: Um, and that’s where I think language and bots are going to be huge. And allow us to like disconnect from this like addiction box. And this thing is so addictive cause we were so successful in the last 10 years of social technology and dating apps. Like the swiping is an addiction fueled machine, you know what I mean? And like I think, that needs to go away. Because that’s causing a lot of the mental health issues. Um, and it’s not anyone’s fault, it’s just the reality.

Laurie Segall: Although you gotta be careful with something like this because it could enable you to talk to like, you know, I don’t even respond to people, it can enable you to talk to like hundreds of people within like seconds, like you talked to, you talk about coming back and having like, you know, all the messages of women telling you what hike they were on? Like you could be doing that in like miliseconds. We talk about, like, the power of this going viral

Shane Mac: Totally.

Laurie Segall: Like, is that good? I, I don’t know. Like.

Shane Mac: If, if it’s disclosed and both sides are using the technology.

Laurie Segall: Right.

Shane Mac: I think the thing that we’re focusing on and the whole idea started as a witty bot on both sides, right?

Laurie Segall: Right, sure.

Shane Mac: And then we built half of the product and realized that it had like a super power that was kind of like, controversial. Um, and so I just think disclosure’s the thing that’s going to be the most important. There’s so many privacy and legal things that are not figured out in this space. When you can analyze every person’s feelings and the words they say, it’s insane. Right? For messaging bots, for messenger, for Facebook, all of us in this space, there’s no laws around this yet. There’s gonna be regulation.

Laurie Segall: I was about to say what do we even need to think about, like I can’t even imagine the privacy implications. If you knew, if you could analyze like my mood, my feelings, these deep rooted things about me like,

Shane Mac: Yeah that a, that ad network is worth way more that Facebook’s.

Shane Mac: its funny, the day we built the keyboard Stefan and I were driving in a Lyft to the Battery. And I recorded this moment cause on the radio, it, a, uh, I’m not that religious but I kind of believe in like spiritual and fate and whatever, and on comes Zack Brown Band and it’s like “I love her so much but I couldn’t find the words to say.” And I was like holy shit that’s what our keyboard is. It helps people find the words to say when they don’t know what to say.

Shane Mac: And I was like, this could be used for anything, this could be used to help people know how to communicate with their family or know how to communicate with a spouse or, you know, if I could build a relationship keyboard for people in relationships that helps them communicate with more affection and more empathy, or ask better questions like, could that save relationships? And this lady in the front seat she had a speech impediment and she was like, that would be incredible. She was like, if I had a keyboard, my whole life I haven’t been able to get work or jobs or anything because I can’t find the words to say because I don’t really have confidence to speak and I have this big speech impediment and she’s like I would love to have something that would help me know how to say better to my kids just I love them. Or ask them questions that I never would have asked them. And how to reach out to my family and I’ve never been able to kind of find the words.

Shane Mac: And we were like holy shit, and like I was filming it, it was like, this like halo moment. I was like “what is happening in the world?” I was like I just thought we were the worst people ever and now I’m feeling like we’re gosh… er, we’re, or like God’s telling us something, I was just like “what is going on?” Uh, and Stefan was like “This is really big.” And .I don’t quite know what going to happen with the space, but language drives the world, it trains our brain, it’s what wires humanity and if software can create language for moments and situations that teach us all how to be better versions of ourselves. I believe it’s going to have massive impacts

I think it’s safe to say this is early phases but imagine what could happen with this type of tech once it evolves. Could bots date for us? Predict our compatability? If our dates are set up by a machine acting on our behalf is it disingenuous? Where’s the transparency? There’s a lot there. But i’ll end on this: as the lines blur between machines and humans i think we’re going to have to ask ourselves a real question, where will we draw the line? We don’t mind if google autopopulates our emails with pre programmed responses, but should you mind on a dating app? It feels a bit dot dot dot right now but i think it’s a conversation worth having. Because in my experience we can’t ignore the edges because the edges always become the center. Before we know it tech is just an extension of us complicated humans. 

I’m Laurie Segall and this is First Contact. 

For more about the guests you hear on first contact sign up for our newsletter, go to firstcontactpodcast.com to subscribe follow us on social. I’m @lauriesegall on instagram and follow our show, we’re just in the beginning phases so we need all the followers we can get. We are @firstcontactpodcast. Subscirbe to First Contact on the iHeart radio app, on APple podcasts or wherever you get your podcasts. 

First contact is a production of Dot Dot Dot Media executive produced by Laurie Segall and Derek Dodge. This episode was produced and edited by Martin Burgess, our engineer was Emily Marinoff, original theme music by Zander Singh.

Visit us at firstcontactpodcast.com