Tech Brew Ride Home - (Bonus) The Superhuman Brouhaha With Mike Davidson

Episode Date: July 13, 2019

Remember the whole Superhuman kerfuffle of the last week or so? Mike Davidson wrote a blog post calling out some shady stuff in the Superhuman email product, all of silicon valley debated it, Superhuman walked things back a bit, and actually, I didn’t mention this, but Mike had a second post about this, which was even more in depth an eloquent than the first one. So, I reached out to Mike to talk about this whole thing, not because I wanted to re-litigate it, but because I wanted to poke at… well, what I said last week… what does this whole debate say about the discourse in tech at the moment? Mike's 2nd post on this that I didn't mention on the podcast Sponsors: Wix.com/podcast Capterra.com/ride Learn more about your ad choices. Visit megaphone.fm/adchoices

On April 4th, 2023, around 2 in the morning, a man was found stabbed multiple times on a sidewalk in downtown San Francisco. Hey, who did this to you? What happened next turned the story into a political firestorm. Reports have identified the victim as Bob Lee, the founder of Cash App. From Bloomberg Podcasts, this is Foundering, the Killing of Bob Lee, beginning April 16. Welcome to another weekend bonus episode of the TechMeme Right Home. I'm Brian McCullough. So remember the whole Superhuman kerfuffle over the last week or so.

Mike Davidson wrote a blog post calling out some shady stuff that he saw in Superhuman's email product. All of Silicon Valley debated it. Superhuman subsequently walked things back a bit. And actually, I didn't mention this on the show, but Mike had a second post about this. which was even more in-depth and eloquent than the first one. Link in the show notes. I reached out to Mike to talk about this whole thing, not because I wanted to relitigate it,

but because I wanted to poke at it in the way that I wanted to poke at it last week. What does this whole debate say about the discourse in tech at the moment? Mike was, true to his original posts, thoughtful, eloquent, and really interesting about this whole thing. Please enjoy. Let's start with this. ever had anything that you had written online sort of go viral like that or whatever?

Yeah, I mean, I used to write a lot more on Mike Industries over the last, let's say, 10 years or so I've just been writing less and less. And, you know, I kind of, you know, I blame myself a little bit for that, just kind of being lazy. And I also blame Twitter a little bit because, you know, every time you have a thought that you want to get out there in the world, you can, you know, you can spend a proper three or four hours writing an argument about it and writing an article about it. Or you can just spend 10 seconds writing a tweet about it and move on. And it's kind of like a pressure release valve for your thoughts.

Well, and actually, you know what? Maybe this is important too, is to do the timeline. Like, you actually, didn't you tweet about it first? I did. Yes. I mean, I, so this issue actually goes back quite a ways. I believe I did onboarding or I almost got through onboarding. on superhuman, maybe in January or something like that. And I stopped halfway through onboarding when I found out about this privacy issue. And I found out that you couldn't even turn off images in the clients. So I was like, you know what, guys? I don't want to be part of this.

And then... Did you actually specifically express that to them? I did, yes. To the agents that was helping me through the white glove onboarding or whatever it's called. But I did express that. And then I tweeted about it with a screenshot of superhumans kind of sales pitch for read receipts. And the tweet said something like, you know, this is why you should turn off images in your email client. And the, you know, the CEO responded not to me, but to somebody else who responded to my tweet.

And the CEO basically said something like, well, you know, we should probably require people to allow themselves to be. tracked if they want to track others. And if they want to turn that setting off, they should also turn it off for themselves. And when he said that, I immediately recognize, oh, that's the rule that LinkedIn uses. And if you think about LinkedIn, they have that one feature of the service where you can see who has looked at your profile, right? Right. Right. But, but in order to see, famously, even Facebook has never allowed you to do. Exactly. It's a really good point. Facebook hasn't allowed you do that. LinkedIn does allow you to do that. So you can say, oh, you know, 10 recruiters looked at my profile and like this CEO looked at. It's kind of useful. Like,

it's cool. But if you want that functionality, you have to also make yourself visible when you look at somebody else's profile. So you will show up. So like, you know, I have product design complaints about LinkedIn, but like that is actually a pretty well considered rule that they have. And so, you know, Raul used to work at LinkedIn. And he probably saw the analogy of like, oh, LinkedIn does it this way, we should do it this way too. But as you and I both know, the reason that doesn't work with read receipts is there is no way for the person on the other end to opt out globally. And that's the problem. All right.

So you said you almost didn't even publish this as a blog post. Yeah. So I, you know, I had a few spare hours over the weekend. And I just kind of sat down on the couch and started writing. And, you know, before I knew it, I had 4,000 words sitting there. WordPress and, you know, I read it over a few times and was like, you know, I felt pretty good about it. But then I thought to myself, like, is this, is this fair? Am I being fair? Am I making an even-handed argument? Is this important? Have enough other people written about this already? You know,

so I sent it to three people that I trust. And I was like, hey, should I publish this? Like, is this, you get anything out of this? And all three of them were like, you need to publish this. So, you know, whatever it was, Monday morning or Tuesday morning, I just hit the publish button. and bingo bingo it kind of just like flew around the internet well and walk me through the reaction to that like um what came first the people being like exactly or the people being angry about it uh wait what's the difference between those two people right right right the the people i'm saying the people being like right okay so the people being like yeah i'm pissed about this too or the people being Hey, how dare you criticize this startup?

Oh, by far the former came first. I mean, it was a barrage of, I can't believe this is happening. I can't believe companies are doing this. I can't believe nobody knows about this. Like that was, you know, I think for the first few hours, that's kind of all it was. And then, you know, when it got around to sort of like, you know, the ad tech people and the kind of venture capital people, you know, people that sort of know, people that sort of know about. this world of data targeting, that's when you got some of the defense kind of coming in. So, you know, if you do like a search on Twitter, even right now for that article and look at the kind

of ratio of like, this is terrible versus like this is okay, you know, it's massively, massively weighted towards like, this is terrible. Okay. So, you know what, that's kind of why we're talking, because I kind of want to poke at that. But let's put a pin in that for now. Sure. because and and put a pin in that by by keeping in mind that what interests me about that is maybe this idea that there's a certain way of doing business in Silicon Valley that is over

and people haven't made their peace with that yet but okay what is your personal take on why it hit a nerve i think it hit a nerve because it's a technology that people deep in the know have known about for a long time, like not a year, not five years, probably more like 10 years, and have been using in increasingly invasive ways over the last 10 years. And so for those people, this is like nothing. This is like seeing the sun come out every day, right? It's not surprising. And I think what those people forget is that the world is not nearly as educated about the way, you know,

ad targeting on the internet works as they are. And so, you know, when you see these, these, you know, and it's funny, it's not just like a people in tech versus people that aren't in tech. That part was obvious to be from the start, right? Like, there are some people in tech who know how this works. And basically nobody who isn't in tech knows how this works. That was obvious to be from the start. But what became very clear in this debate is that a lot of people in tech, we're talking engineers, CEOs, designers, PMs, like had no idea. that just opening an email could reveal and was in fact revealing your location to somebody else unbeknownst to you. So, you know, it was the fascinating thing to me is like this is a technology that has been like out in the open forever and has been openly abused by the people who know how to use it best, really behind the back of most of the world.

Right. So to what degree do you think that this was people being like, oh, we thought email was somehow like kind of pure. than the social media panopticon and and like having the scales for all from their eyes? Well, you know, pure, I don't know that I would call it pure. I would just say like people think of email as a kind of a one to one thing, right? So like if you get an email from your grandmother, the communication is between your grandmother and you. If you get an email from your boss, the emails between your boss and you, pretty much everything

you do on Facebook, you know, is between you and Facebook and whoever. they want to license your data to, right? So, like, I think it's the personalness of email that sort of like, it surprises people that there's this kind of like man in the middle who's doing untoward things with, you know, with your data. And, you know, I just got finished with an episode today talking about like the whole Zoom thing. I don't know if you've been following that. So it was fascinating to me that that happened right after this because the reaction was not the same. You know what I mean? Like, in a sense, it's not, it's not apples to apples, but Zoom was doing something sort of shady in the background. They got caught. But people didn't have the same jump to

the defense of Zoom reaction as they did to superhuman. Well, I think there's a couple reasons for that. Like, number one, you know, when I first read about the Zoom thing, I was like, oh, you know, honest bug, right? Like, bugs happen. Like, I don't, you know, I don't expect everybody to write perfect code and you know my first reaction was like oh that's a really bad bug um but then the more you read about it you're like oh they installed a web server on your machine just so you wouldn't click i have to like make an extra click that's actually a security feature that apple put in like that's bad um so so i think you have to read a little bit about the issue to even know that it was sort of um you know a highly negligent thing but the the the thing on top of that though is i think that your next thought is

have I ever been burned by this? And the answer is no for the Zoom bug, right? It's like, have I, has my camera, have I ever been using my computer and been auto joined into a meeting full of strangers? Like, no, I haven't. Like, 99.9, possibly even 100% of people in the world, weren't

affected by that bug. But if you think about email and you think, oh my God, any email that I received from superhuman, or frankly any of these other services like Mix Max and HubSpot and whatever else, like any email I've got, I mean, over the last, you know, however long year, two years, five years, could have been location track. Then you actually don't know how many times you were exposed.

Playing devil's advocate a little bit. Some people's reaction was knee-jerk. Like, this guy is just targeting a startup because they're successful. Like, what would your take be? Like, if you had posted this before Superhuman raised that round and sort of Supergoman got on everyone's radar, although they were on people's radar before, but like, do you think that it would have hit a nerve prior to that? Or was it like, okay, these guys are on everyone's radar, and so that kind of helped it kind of gain steam? No, I think it would have hit a nerve before the

funding. I don't think the funding had anything to do it. I don't think the funding had any to do with it. I think the article had something to do with it. I think actually sitting down and reading what this technology does and how it was purposefully put into this app that claims to be a, you know, and of great design, like, that's what really, that's what, that's, that's what hit a nerve with people. It wasn't really the timing of it. I do, you know, I do take that criticism seriously, however, like, the only, and I just want people to know, I mean, the reason why this is, this is, this became important to me in the first place is, like, I'm a designer, like, design is my beat. And when, when, a, when an app or a company comes to town and, and, and pitches themselves as, like,

you know, purveyors of amazing design. And, you know, I, I want to look at it. And I want to judge for myself whether that's true or not. It's kind of like, you know, imagine if you had a, you know, a dry cleaner come to town and a dry cleaner said, hey, we're eco, we are the most eco-friendly cleaner in the world. And we want to dry, you dry clean your clothes in the most eco-friendly way possible. And then you, you know, you're like, okay, that sounds great. And then you drive by one day and there's like black smoke, you know, coming from the top of the building. and you're like, wait a second, what's going on inside this dry cleaner?

And then you find out, like, lo and behold, oh, they use formaldehyde and they use, like, all these other chemicals. So, like, yes, all of the companies that do this sort of thing deserve this sort of criticism that Superhuman is getting in that article. But Superhuman is the one putting themselves out there as this company that really cares about great design. And so I just felt like I had to call bullshit on that. Today's episode is sponsored by Wix.

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We all have that friend who's the first one to try things, whether they're just super trendy or more of a guinea pig. When you're making a choice, it's always nice to hear it from someone who's been there, done that. Choosing the right software for your business is no different. You can read thousands of real software reviews to help you choose the right software for your business on captera.com slash ride. Captera is the leading free online resource to help you find the best software solutions for your business. Yeah, so I think I mentioned to you before we spoke that like we sort of hit on the same analogy.

Like the point that I made when I was talking about this last week, I also use the think different thing. Do you go all the way back to Starwave? Is that way you know Mike Slade? Yeah, absolutely. Yeah, okay. I actually joined that company right after they stopped being StarWave. So they were, you know, the Walt Disney Internet Group or I think that was the name of it when I joined.

But yeah, same company. Okay. So the point that I tried to make was I felt like some of the reaction was like, wait, we can't do creepy surveillance stuff as a business model anymore. And people were pissed about that. And it's like the point I tried to make was, no, you can't because Facebook and Google have made their mistake. Now, they can still do it because they've got these platforms that people can't quit. But if you're a startup that you have to prove yourself to people, you can't. And you have to know that.

And, like, that's the biggest mistake. If you can't know that you can't get away with that as a nobody startup, that you don't have the juice to do that. And also, that's aside from the morality issue of doing that sort of thing. Like, that's the sort of thing that I was like, yeah, think different. Like, you can't, the old business models might not. work anymore. Right. And I totally agree with everything that you just said. And on top of that, I would say, even if you can, why would you want to? You know, like you have this opportunity

to be a privacy focused email client that does all of these amazing things that people seem to love. Like I still haven't used superhuman and I never will. Don't want to. But, you know, from the demos I've watched, like it does a lot of really cool stuff. Like people enjoy being able to do things like, you know, automatic, they have this automatic intro thing where, like, with a couple of keystrokes, you can set up a standard mutual intro between two people. Like, that's really cool. Like, if you, if you want to be known as an email client that is doing things different, that is thinking different, why would you automatically go towards the worst practices that have sprung up? Well, and that's the point that I was trying to make is it's

lazy. It is. Again, okay, the last generation of startups, they, they get scale, they have a billion users, and then they're like, well, how do we make money? We strip mine people's data. So in the new generation, the way to differentiate is to, you don't win the new war by fighting the last war is the stupid analogy. But like, there is an opportunity here for startups to be the new sort of startup, the new sort of philosophy. Like, remember when Google was thought of as, like, genuinely don't be evil, like the

alternative to Microsoft? Yeah, yeah. I don't know why people don't see that that is a, just a blaring neon sign that's like, here's a way to differentiate, you know? Yeah, yeah. No, I think they will for sure. And I don't know if it's going to be superhuman that does it. I mean, I hope it is.

Like, I don't have anything against those guys. I don't, you know, I don't care if superhuman becomes a $0 company or a $100 billion company. Like, literally doesn't matter to me. But, you know, I would like to, if they win, I would like to see them win on a good ethical playbook. And, you know, I looked at the. their privacy policy, their new privacy policy. I guess the Wall Street Journal just picked this up yesterday, in fact. They've just changed their privacy policy,

and they've now explicitly included in their privacy policy and ability to sell data to data brokers. And, you know, it reminds me of my favorite quote from Anil Dash, which is, if you use the word optics and you're not making telescopes or glasses, you're probably doing something awful. And I kind of feel the same way about the term data brokers. I'm sure there are some reasonable data brokers out there,

but when I hear the company is interested in either buying or selling data from data brokers, my mind immediately goes to bad places, especially if it is a company that wants full access to my corporate email account. What is your take on superhuman's response? I don't know if they've – I'm not trying to out anything or whatever. but like did they reach out directly, but not even that, like their public response and how they have dealt with with this whole brouhaha. Yeah, I think they, I mean, they haven't reached out directly to me. Some people associated with them have and I've had some private conversations with them.

And that's fine. Like, you don't need to apologize to me. Like, I don't, you know, I haven't been hard. No, and I wasn't even suggesting that. I was just like, but your takeaway from their response in the sense of what we just been talking about, like this new way of like, oh, the rules have changed. The game has changed. We got to evolve along with it. What do you think of their response to this? Yeah. I think their response, like on a, if I was going to grade their response A to F, I would grade it, you know, I don't know, C minus, you know, like it was, I think they closed the, the most dangerous hole, which is, which is showing your location. So, Bravo. I mean, if you read my follow-up article, I give them points for all the things that they did. But I still don't think they have internalized the idea that serptician, collecting data on people in a way that frightens them and reporting it back to others

is a bad thing. And so I'm very, I guess, disappointed that they didn't take the opportunity to say, oh, you know what? We didn't think about this. We're turning off read receipts. We want to be the email client that cares about your privacy. I mean, it would have been so easy to do. And even today, even after the second article, it would be so easy for them to say, you know what, we want to be the email client that cares about and respects your privacy, and therefore we are not only turning off read receipts, removing them from our product, but we are protecting you from other such read receipts. I wrote a copy for them, even.

So anyway, it's something they have to decide if they want to do on their own. But, yeah, I don't know. I'll give them a seat. You wrote, I think, somewhat eloquently about this in your second post, about how you're sort of privileged enough to deliver this message, to allow people to take what you said seriously. Like how much, to what degree was your post taken seriously because you are who you are? You've been a successful founder with successful exits and things like that.

And so how much of the blowback was maybe about, there's like this mindset that it's like fight club. You can't speak ill of other startups once you're in the club. Do you know what I mean? I do. So that's kind of a two-part question that I didn't even frame, but to what degree are you privileged to deliver that and other people wouldn't have been able to deliver that?

And to what degree is the pushback? How dare you speak ill of another startup? Because you were successful, so you should be on board. Yeah, yeah. I mean, I think it's a good question. I think the soapbox that I have is a very privileged one for sure. I don't need to worry about, you know, my boss firing me for my job. He and I have a great relationship.

I don't need to worry about my reputation in the industry. I've built up a reputation over my entire career that I'm proud of. I don't need to worry about being blackballed. I've got plenty of great relationships with investors and whoever else I may want to work with, many of whom who have DM'd me, in fact, over the last week or two. So I don't have to worry. I don't have a lot to lose, I guess, which is a big, you know, which is a big advantage. However, you know, there was a part of me that, you know, that first night,

after I wrote the article and it kind of blew up, there was a part of me, like, when I went to sleep that night, I did kind of think to myself, like, what's going to happen to me tomorrow? Like, what's the, is somebody going to, like, stage a big PR campaign against me tomorrow or something? Do I have to worry about that? And, like, it didn't happen, you know? So it ended up being, you know, a concern that that didn't come to fruition. But like, you know, I don't think most people are in a situation where they can do that. I think people have to worry about, I think most people, you know, worry about, hey, what, am I ever going to be able to raise money again? Am I ever going to be able to work in tech again? You know, so you've got to be careful. So, you know, I fully recognize the,

the rarity of that situation. But I also feel like it's my responsibility to use my privilege to speak out against issues like this for people who don't necessarily feel safe enough to do that. Now, to the second, to your second question, which revolved around like how much of the backlash is related to this, I would say not much, really. I think most, I think almost all of the backlash was essentially just people who are like, hey, this technology's been out in the open forever. And now you're telling us we can't use it. Like that was really the, that was really the majority of the backlash. And you know, if you, the, the, the furbidly, you know, the, the, the furb you dig, the more you realize how many companies trade on this sort of data. Like, you know,

there's the, there's the major ones like, you know, HubSpot and, and Yes, Where and, you know, Mix Max. But like, there's probably a long tail of companies that have been accessing this data for a long time. And this whole industry, I think, for the last, you know, five, ten years is probably like, I hope nobody finds out how creepy this is because we're able to make a good amount of money on it. So, yeah, I don't know. Oh, by the way, I think another, another aspect of it, too. is, you know, how many other investments out there and how many other startups out there are using data in a way that if the New York Times reported on it tomorrow, it would make them look bad.

Which is why people are DMing you and not talking to you publicly. Exactly. Exactly. Well, also, it's a weird thing, like, because I spoke on the show about how, like, I bailed out of the onboarding because I was like, I don't have, I don't have a freaking hour to give you. Yeah. Like, so I've never understood like all of these, you know, all my VC and founder types that have no time in their day or week.

How did they find an hour? Like, I found it. The one thing that I've found weird about superhuman and I haven't used it and people I trust seriously swear by it. So I'm sure it's a great product. But they have pursued this very obviously. It's sort of like a cool kids club thing. Like one day you woke up and every VC and founder type that you knew. there was that little scent from superhuman thing on there.

And like that's, I don't know. Like so it's weird that it worked out this way because like that's sort of the thing. It's like, well, we get all these, we get all the cool kids on board with us. And like, does that protect us and things like that? I don't know. It absolutely protects you. Yeah. That's exactly what it is.

I mean, it's having a lot of powerful people using your product. It's having, I think, 120 of the most connected angel investors putting money into your company. Look, if I was an angel investor and superhuman and I wrote that post, I probably would have received a check for my money back the next day, right? Like, and maybe not even that. Maybe like you're off our cap table, screw you. Like, you know, but I was able to write that post because I'm not financially involved in the company. And so, you know, if you look at all the people, well-meaning people who probably agree with me who are involved in the company but can't say anything, you know, it's probably a lot. I will say this, though, I want to, since you mentioned the white glove onboarding,

And since we're talking about product design, you know, that is actually, you know, it's weird. But there's actually some wisdom to that approach. And it was an approach that I actually pitched at Twitter at some point, believe it or not. Oh, God. Yeah. Yeah. So imagine this. So we have, you know, obviously we onboarded a ton of more people at Twitter, you know, millions a day, right?

So it'd be a lot harder. But one of our biggest problems at Twitter, which remains to the day, is taking somebody from not knowing how to use the product and not knowing the value of the product to having like an amazing timeline and amazing experience and knowing how to DM people and knowing how app replies work like shortening the time from you know that beginning state of knowing nothing to that end state of having a perfect setup and i remember going to my boss at the time at a messenger who was the cptio and i said look wouldn't it be great if we could do like a just a white boarding on a white glove onboarding session with a small number of people and show them exactly how to use the product over an hour,

how much would we then learn about how we should teach people about this product? So the goal was never to do that with everybody, but if you can do that as part of your user research, you might figure out kind of what are the things that are most confusing about this product and how can we most easily explain them. Well, listen, Mike, I've literally done that for people where it's like, okay, I'm going to explain to you why Twitter is useful for you. I know you're into baseball.

I know you're a little bit into politics. I'm going to make a list for you of these 50 accounts to follow. Just follow them and get back to me in a week and you'll get it, right? Yeah. It's literally that simple. But it's not that simple because you can't do it at scale. Right. All right.

So let's wrap up. Is there anything? What's your major learning or, if there is one, about this experience? Does it say something to you about startup culture at this moment? I think this issue is going to pivot

more quickly than we realize. I think over the last few years, the things that we've started to do with data have crossed the line. And I think the companies that will be ahead of the curve are the ones that recognize that and start to protect their users

against this sort of abuse of data. And again, I feel like superhuman and every other company has the perfect opportunity to do this right now. So I think, I think, like, that's one of my learnings, is that like, we are right at the fulcrum of privacy becoming a major, major selling point in devices, in services, in companies. And so, like, I think that's learning number one. I think, you know, learning number two is there's this vast sort of world in, it's not just

in Silicon Valley, but just like in the kind of growth startup space where, you know, people are too afraid to kind of say the emperor has no clothes. People are too afraid to sort of call out bad practices when they see them because they are very concerned about, you know, am I associated with this bad practice in one way or another? Have I used, have I committed this bad practice in the past? Do I have investments in companies that do things like this? And so, you know, a lot of people just clam up and say, okay, well, I'll just wait for other people to argue about this and see what happens. And so, you know, I think if we were honest, if we were more honest and open about what we see in the world of startups and how people are making these sorts of ethical or unethical decisions, we would probably end up with a lot better products.