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Learning from successes and failures: This week Paul Ford and Rich Ziade talk to Michael Sippey, whose career spans the history of the web—from blogging pioneer to Six Apart to director of product at Twitter to startup founder. He details his work at Twitter during a time of transition for the social network, and then shares frank perspectives about launching and recently shutting down his startup, Talkshow.


Rich Ziade: Paul Ford!

Paul Ford: Richard Ziade.

Rich: This is a big day.

Paul: Well, people can’t see why.

Rich: Well first off let’s tell people what this is. This is Track Changes. Welcome to Track Changes.

Paul: The official podcast of Postlight, a digital product studio in New York City. We make your apps, we make your platforms, we make your websites, and we’re good at it.

Rich: Damn good at it.

Paul: Real good at it.

Rich: Yeah.

Paul: And we are talking to you from our offices on Fifth Avenue in New York City, very close to Union Square Park. And we are talking to you from our very own brand-new podcast studio.

Rich: Boom.

Paul: We are in our office, there are a lot of books here, we’ve hung some curtains, there’s a plant. There are people walking around outside. I can actually hear boots, so if you hear that, it’s not someone creeping up on you. It’s just the sound of digital products being built at a digital studio. And also probably somebody getting a Diet Coke out of the fridge.

Rich: Or a pretzel.

Paul: Yeah. You won’t hear the chewing, because we did that level of sound insulation, but.

Rich: Yeah.

Paul: It’s an old building with creaky boards.

Rich: Yes.

Paul: So Rich, there is somebody very special on this podcast today.

Rich: Tell me. Talk to me, Paul Ford.

Paul: Michael Sippey.

Rich: And when you say Sippey you mean…Sippey.

Paul: S-I-P-P-E-Y.

Rich: Right.

Paul: So first of all, we have to ask him about this, but this might be a person who may be the first blogger.

Rich: Is that true?

Paul: It’s actually real. And, yes, we do tend to talk a little bit too much about the olden days of the internet —

Rich: I, yeah.

Paul: But Michael has recently been through the full intense startup experience.

Rich: Yup.

Paul: And in the meantime he was VP of Product of Twitter.

Rich: So he’s seen it all.

Paul: He’s seen, literally, like, the thing.

Rich: Right.

Paul: He’s stared into the maw of the beast.

Rich: Right.

Paul: So, let’s get him on. He is joining us via Skype. This is our first ever Skype podcast.

Rich: Don’t hype this up. We’re a tech shop, dude. Don’t hype it up too much. Skype should be like a totally casual thing for us.

Paul: Seriously, plugging wires in — I would much rather build a REST API than plug wires into boxes. [laughter] Everything goes wrong. Hey Michael Sippey, are you on the line?

Michael: I’m on the line. There was, there was, the Skype noise happened, there were buttons that were pressed, and I’m here now. It’s very exciting.

Paul: It’s really exciting to have you on. So is it fair to say that you were the —

Michael: Wait a minute. Wait a minute. First thing. Honest to God, first Skype interview?

Rich: Yes.

Michael: Incredible.

Paul: Yeah.

Rich: I mean…

Michael: So you guys actually have, like, microphones when you do this?

Paul: Oh yeah we’re all set up.

Michael: Like with people that are in New York?

Paul: We’ve been going to a studio and recording and we decided when we moved to our new office that we would build the podcast studio out in the office.

Michael: There you go.

Paul: Since we do it all the time. It allows us to be a little more flexible and casual, so this is our first in-office recording. Tom, Tom Meyers has built us this studio.

Michael: That’s awesome.

Paul: It’s pretty cool. So, Michael. Welcome. Is it fair to say you were the first blogger?

Michael: No. It’s not fair. It’s…I think it’s fair to say I’m one of the first, I don’t know, 15 or 20. There’s Scott Rosenberg, who is a great journalist and writes for Backchannel, did a book about blogging, back when books about blogging were a thing. And not just, like, the here’s how to have a great small business blog that will drive all of your SEO for you forever. He did a history of blogging and kind of what it meant for journalism. And so yeah, there’s a chapter in there about the early days of blogging and, you know, I’ll give credit to Dave Winer and Jorn Barger and all those guys. But yeah, probably one of the first, I don’t know, dozen or 20, something like that.

Rich: That’s still pretty damn amazing.

Michael: Yeah, I guess so. I mean basically, like, I wanted to learn HTML, and I was an English major, and I figured out, like, I had been sending email to friends that had email addresses — this was the mid-’90s — and wanted to figure out how to put stuff on the web and so I started to put up, I guess what we’d call now hot takes on media and technology and culture back in, like, ’95, and then started to do link blogging in ’96, and …

Rich: Wow.

Michael: Something like that. So it was, yeah, very early.

Paul: One of the things, one of the things you did that was, I remember really specifically, is that you had a feature called “Just One Question.”

Michael: Yeah.

Paul: Where you would ask someone just one question. And it was clever and fun and short, and this was also kind of the age of things like Suck were happening, and there was an editorial sensibility in the new medium. And I always sort of felt that you were one of those people that brought a sense of edit, a sense of writing, and a sense of craft into this medium where it actually just hadn’t existed before. It had been weird FAQs and, you know, pages about mushrooms and llamas. And suddenly there were these voices that popped up.

Michael: I really wanna — go ahead.

Rich: For context, Paul, what number are you?

Paul: Oh I was in, I don’t know. I couldn’t tell you. I mean…

Rich: You were in the hundreds.

Paul: I started writing online in ’97, so.

Rich: OK. That’s when I started, actually, but nobody read my stuff. Everybody read your stuff.

Paul: No early, I would say I had 50 readers a day for three years.

Rich: OK.

Paul: Yeah.

Michael: So let’s fast forward. So Michael’s going …

Rich: I want to hop — I want to hop through Michael’s life.

Paul: Yeah let’s do that.

Rich: Can we do that?

Paul: Let’s do it.

Rich: Michael I’m going to throw out a year.

Michael: Let’s do it.

Rich: And you tell me where you were and what was going on in…

Michael: Oh god.

Rich : 300 characters.

Michael : OK.

Rich: OK?

Michael: This is good fun, I like this.

Rich: ’99.

Michael: ’99. ’99. I was working for Viant, which was an internet consulting firm, kind of at the height of the dot-com craziness.

Rich: OK. 2002. Viant’s gone. I don’t know who Viant is, but they’re gone. [laughter]

Michael: Viant’s gone. Yeah, they were gone. So Viant, Viant is gone by then. I left Viant in 2…beginning of 2000, seeing the kind of writing on the wall.

Rich: Mmmm hmmm.

Michael: I was working with some friends on an email services startup called Quris. The best part of the company was the team. I was working with great people like Heather Champ and Leslie Harpold and Gina Lambright. Just really fantastic people. And doing kind of crazy, complicated email programs for Charles Schwab & Company.

Rich: OK.

Paul: So the early days of internet advertising and marketing.

Michael: Yes.

Paul: OK.

Michael: Very early days. And I was also raising, at that point, 2002, I was raising a two year old.

Rich: Oh wow, OK.

Paul: And I know for a fact you went and got an MBA somewhere along the line. Did you have it by then?

Michael: I did have it by then. I got that, I graduated from Haas in ’98. I’m older than many of your listeners probably.

Paul: So are we.

Rich: 2005.

Michael: 2005 I was working for Six Apart as VP of Product, working on Movable Type and TypePad.

Rich: Oh wow.

Michael: And we were probably working on building Vox at that point.

Rich: Oh OK.

Paul: Which listeners may not realize has nothing to do with Vox Media.

Rich: Nothing to do with it.

Michael: Right.

Paul: The maker of —

Michael: Nothing — there were no explainers on Vox.

Paul: No explainers, no cards. What was Vox? It was a…

Michael: Vox was a blogging — Vox was a blogging social network. Essentially friending —

Rich: I couldn’t understand it. I remember it, I didn’t understand it.

Michael: Friending and following and, essentially we were trying to…we were trying to make blogging simpler, and accidentally made it much more complex.

Paul: So I mean this was a world of…Six Apart with Movable Type, TypePad, Vox.

Michael: Yep. And LiveJournal.

Paul: And LiveJournal.

Rich: LiveJournal.

Paul: So — no but at that point, that was, it all seems kind of small now because of things like Facebook —

Rich: Right, that was the world.

Paul: But that was the internet. Those were the…so you were a leader at a place which had four of the largest platforms online. Well three, plus Vox.

Michael: Three plus Vox. Exactly. Three plus Vox. [laughter]

Paul: Sorry.

Michael: Totally fair.

Rich: 2011.

Michael: 2011 we had sold Six Apart, I was working for Say Media. We had sold Six Apart to VideoEgg, we had renamed the company Say Media, and we launched xoJane with Jane Pratt. So I was working on it with Jane Pratt at the time, which was a blast, as well as Ted Rheingold. We had bought Dogster and Catster, and we were essentially trying to build a new media company.

Paul: You made all of that up. None of that —

Rich: Making up words.

Paul: Yeah.

Rich: Didn’t expect that for an interview.

Michael: Totally.

Paul: I got to say, Michael, when somebody says “VideoEgg” I get, I get a bad feeling. [laughter]

Michael: I think that’s why we renamed the company.

Rich: 2014. We’re getting it close. 2013. Let’s tighten it up.

Michael: 2013 I was working at Twitter, running the consumer product team and the design team, and doing crazy things like working with Tom Hoffman on Vine and managing a big team.

Paul: Michael was it, you were there during a complicated transitional moment, right? Like, it was going public, API services were being taken away…pause.

Michael: Pause. [laughter]

Rich: How big did your team get, Mike? First off, is it Michael or Mike?

Michael: I enjoy, I enjoy Michael.

Rich: Michael.

Michael: It was a big era of transitions. We were making changes to API policy, we were bringing new tools for publishers and developers to Twitter in terms of cards. I think the most dramatic thing we were doing is really shifting the whole company to kind of mobile-first development. So that was the, that was the biggest shift that was happening.

Paul: Now at that moment, which now feels about seven or eight thousand years ago, but was really not that long ago, you had, at that point, a decade-plus dealing with social self-publishing behavior online. And it struck me as an outside observer, and I knew you a little bit at that point, that no one had prepared for what had just happened. Like it just was an explosion, especially as mobile started to happen, that there weren’t even any conceptual frameworks for growth of that kind.

Michael: Yeah. I would, I would completely agree with that. Basically everyone was inventing everything as it happened. So everyone looks at both Twitter and Facebook and kind of everything that’s happened since YouTube, Google, as, you know, there was the kind of fait accompli, like there was this master plan, and of course everyone’s just essentially building against a roadmap that was already defined, but that’s really not the case. Like there’s…

Rich: Everyone’s winging it.

Michael: There’s just, everyone’s winging it all the time.

Rich: Yeah.

Paul: What is it like going into an office when you truly have no idea what’s about to come down the pike, in a situation like that? I’ve never had that experience.

Rich: And Egypt just fell. That’s the other thing, right? It’s, you’re coming into the office and it’s like “Oh where do we take this technology roadmap?” But like, the Middle East has fallen apart because of your product.

Michael: Right. It’s, I always talk about, like, I spent two years at Twitter, and I talk about that being essentially like being in a hurricane. Where it’s like, weather, you know you understand what weather is. But now it’s like it’s weather you’ve never seen before, at a, with force that you’ve never seen before, and it’s chaotic. There’s shit flying all over the place. You’re essentially trying to keep, you know, the house together. And then there’s a newscaster out front trying to essentially make sense of it all and kind of tell the story. And occasionally you’re in the eye of the hurricane and it’s nice and blue and skies are blue and it’s sunny and beautiful. And then the other half kind of whipsaws you in the other direction.

All you’re trying to do though, is like, you know, when that stuff is happening you…you just go to work. I mean you just go to work. You go and you have a schedule and you meet with your team and you’re trying to ship good product, and you’re trying to make the right decisions, and you’re thinking about where the product is going and where it is and how you can make it better and you just get to work.

Paul: And occasionally the windows just blow out mid-meeting.

Michael: Yeah. Occasionally the windows blow out mid-meeting. There were a few occasions like that.

Rich: It’s funny that he’s using the hurricane metaphor, when, you know, the Arab Spring…it just makes it sound like butterflies and flowers are coming out.

Paul: Yeah it wasn’t that, though.

Rich: And so it’s…I never understood the Arab Spring, like I never understood the phrase.

Paul: Mmm hmmm.

Rich: I mean I’m Middle — I’m Lebanese, by the way, Michael, and so I kind of have a sense of how that part of the world functions. So it was very strange to hear it as if it was this blooming of… [laughter]

Michael: Right like awakening or blooming or flowers…

Rich: An awakening of some sort.

Paul: Americans, as we really like to think that democracy is going to flower if you sprinkle the seeds.

Rich: Right.

Paul: And I think at that point, technology was the seed. We didn’t like it as much when the Bush administration was spreading democracy. We felt that that was, like there was a lot of complexity in that plan because it involved like a trillion-dollar expenditure, and a lot of lives.

Michael: A lot of tanks.

Paul: Yeah a lot of tanks. Like, we knocked over statues. So that was a big conversation in the world. But I think there this sense that, Oh my God these little phones!

Rich: Empowering.

Paul: Yeah. It was…because we have a very positive narrative, a very excited narrative, about technology. And suddenly you’ve got people rallying against, really, kind of nasty, despotic, horrible leaders. And it felt really good, it was exciting, it was thrilling to watch. And it was enabled by these platforms.

Rich: Michael, tell me, what’s the view from where you’re sitting as that stuff’s happening?

Michael: I’m trying to, you know it’s basically like, you’re just kind of in awe. You’re just kind of in awe, honestly.

Rich: Right.

Michael: I mean, you know, there’s the comms narrative that happens, right? Whether it’s Arab Spring or whether it’s something that happens in pop culture or whether it’s some crazy conversation between, you know, two world leaders or something that happens on your platform. There’s the comms narrative that happens that of course, like, you know this is the, these are the tools, this is whatever. But from an internal company perspective, there are two things that happen. One is, there’s a super sense of pride, right? People come to work every day because you’re working on something that you believe is having a positive impact in people’s lives, and that is empowering technology. That’s the narrative that you believe and it motivates you to, to work hard. And you think about your users, and you think about the things that the product can do in the world. And then the other side is, you’re keeping that, that’s kind of the story that’s in your head, and then the other side is, I’ve got this bug to fix, or I have this spec write, or I have this meeting to prepare for.

Rich: Right.

Michael: And so, you know, holding those two things in your head at the same time is sometimes difficult. So just, the thing you know, our CEO at the time, Dick Costolo, was very very good about like, look, this is all, in the run-up to the company going public, etc., there was a lot of positive press and there was a lot of momentum that the company had. He was very, very good about saying like, “Look, there will be darker days. You can’t believe all the hype. You just have to, we just have to get back to work. You just have to focus on every day making progress against the goals that we’re setting for ourselves.”

Paul: And what is, you’re a product manager at Twitter, which is a pretty big job with a pretty broad mandate at that level. It’s a key role in the org. What is that job? Like what would the job description be?

Michael: So I, my history at Twitter is short, but interesting. I joined as a group product manager at the beginning of 2012 to work on the platform. So, you know the first thing that I worked on was Twitter cards, which are the things that essentially attach content to tweets. So now you see them as, like, story summaries and YouTube videos and etc. and so, that was the first feature that I worked on. And then I became Director of Product Management and then VP of Product Management on the consumer side, and at Twitter there are two — there are probably more now, but at the time there were two product management organizations. One focused on what we called “consumer,” which included essentially everything a consumer would touch, and the developer platform. And there’s the ad side, which is all the monetization products, because that is a whole separate technology stack and separate set of products. So I was managing product managers, and eventually also the design team and the localization, internationalization, international team. But the primary responsibility is the consumer roadmap and organization of the PMs that are building features with engineers and designers every day.

Paul: Now are you coming up with ideas in a job like that, or are you just listening to a million ideas and saying “Let’s do that.”

Michael: Yes and yes.

Paul: OK.

Michael: Some of it’s coming up with stuff, some of it’s listening to a bunch of ideas. Because it’s really, really it’s, the product manager, if they’re any good, is really like, some of it’s like idea generation but a lot of it is context setting. The thing that I always have to remind myself and always work to remind product managers of, is that really, you have, as a product manager, three questions that you need to be responsible for answering, which is: what problem are we solving? Who are we solving it for? And how are we going to measure success? Everything else, like how are we going to solve the problem, how are we going to bring it to market, what are the needs that it has from a feature perspective or a speed perspective, or where should the button go or how should it look or how should the brand work — that is a team exercise. And you’ll get much better results if you involve the team, but the product manager’s job is to set that context of, this is the problem that we’re solving, and here’s who we’re solving it for, specifically, and here’s how we want to measure success. Because if you can set that context and you give the context to the team, the team will produce much better results.

Paul: I have to say, as I’ve grown as a professional and a manager, it’s amazing how much of work truly boils down to simple statements repeated almost daily.

Michael: Mmm hmmm.

Paul: Like it’s, as I hear you say that I’m like, yeah that sounds about right. You would need to do that every day, for every —

Michael: Every day.

Paul: Yeah. Every day you just be like, “Hey guys.” Comma.

Michael: “Remember!”

Paul: Yeah. “Let me ask a question.”

Michael: Right. It’s always about, it’s always about setting that context.

Rich: I think we’re almost up to date. You’ve left Twitter. And…

Michael: Yes. Yes. Oh yeah give me another year. Sorry Rich, that was much more than 300 characters.

Rich: It was a lot more. [laughter] It was good chunk of characters.

Paul: We dove in.

Rich: It was worth it.

Paul: I also just love, I love for people to know what people do all day.

Michael: Literal tweet storm.

Paul: Yeah. [laughter]

Rich: So you leave in, what, ’15? ’14?

Michael: I left the beginning of ’14.

Rich: ’14. And then you do, you take some time off. Central America?

Michael: I took about a year off. [laughter] I took about a year off.

Rich: That’s a good amount of time.

Michael: Yeah I took about a year, it was great. I feel very lucky that I was able to do that.

Rich: What did you do during that? What did you, did you grow, like, hot peppers?

Paul: Or a beard?

Michael: I dropped the kids off at school.

Rich: Mmmm hmmm.

Michael: I picked them up from school a lot.

Rich: Wait wait wait.

Paul: Something happened in between, right?

Rich: Yeah in between dropping them off and picking them up, Michael.

Michael: I did a lot of reading.

Rich: OK.

Michael: I started running.

Rich: Oh, OK.

Michael: And I did some, I did some writing, I did some reading. We did some traveling as a family. I did a bunch of cooking.

Rich: Wow.

Michael: And eventually I got bored of all that and I started to do some, you know, help some startups and do some advising and stuff like that.

Rich: Got it. OK. So we’re, 2015.

Paul: And you’re in the Bay area through all this, too.

Michael: Yeah.

Paul: Like you’re in…

Michael: Yeah. Yeah absolutely.

Rich: Yes.

Paul: At this point you’re in the middle of a pretty intense network. You could’ve gone and done something during that time but you really wanted to have a moment to process.

Rich: Come up for air.

Michael: I needed, I needed to come up for air.

Rich: Yeah. OK so it’s 2015, you took your year off, you’re in great shape, you’re cooking better. [laughter]

Paul: Great relationship with your kids.

Rich: Your kids love you.

Michael: They do!

Rich: Yeah.

Michael: That’s like a minor miracle. One of them is now a teenager. Yeah so I was, I started to work half-time, I did like a half-time job with Ev Williams at Medium. Ev and I had known each other for a long time, obviously through Twitter but also through some stuff at Blogger before, so, and Six Apart days. So I started to do some consulting, and really what was great was I got, he gave me the opportunity to work with a really small team. I got to work with a couple of engineers and a designer and, you know, four or five people, and we had our whiteboard and we put stickers on it, and we decided what we wanted to ship, and then at the end of the week we looked at ourselves and said, “Did we ship what we wanted to ship at the beginning of the week?”

And I realized, that is what I loved. Because I had been, you know, spending a bunch of time on a year off thinking like, Oh well do I want to go get another big job like I had at Twitter? Or do I want to go, you know, there’s a career path in the Valley that goes manager, director, VP, VC, and do I want to go that route? And what I really loved was working in a really small team and kind of getting my hands dirty. And so I started to think about what that looked like.

Paul: Ev put you back in the game.

Michael: He put me back in the game.

Paul: Come on, Sippey, get in here.

Michael: God bless him. God bless him. Yeah.

Paul: Come sit in our five-acre offices and do some work. [laughter]

Michael: The funny thing was, I was actually already sitting in the five-acre office. So my wife is an art dealer and runs her business out of our home in Berkeley. And so I couldn’t hang out at home very much, because she’d be like, “You can’t be watching season 2 of Lost again on the couch.”

Rich: Yeah your time was up.

Paul: Oh so you dropped the kids off at school, and then you had to go find something to do.

Rich: Yeah yeah. Don’t come back here.

Michael: Right. Exactly. So I went, so I was coming into San Francisco and I asked Ev if I could have a desk at Medium and he said, “Well do you want a chair, too? Because that’ll cost you extra.” Um…

Paul: For those who don’t know Ev, that’s like a major Ev joke.

Michael: Right.

Paul: Like that, that’s the real deal.

Rich: That’s really funny in that world. [laughter]

Paul: That is like, actually kind of hilarious.

Michael: I know, right?

Rich: OK so you start camping there.

Michael: So I was like camping out and he’s like “Well why don’t you come help us for a little while.” So I did that for six months or so. Then I decided that I wanted to start a company, and I had a few ideas. One of them was what became the Talkshow product. And just was doing some early kind of sketching and wireframing, and started to talk to my co-founder Greg Knauss about it, and it got him excited and we both got excited. And then we started to build a little bit more and that got a couple other people excited, and they were nice enough to invest in the company. And we started a company, and raised some money, and built a product and launched it, and ran it, and…all of that.

Paul: So wait, what was the Talkshow idea? What was the big idea you had?

Michael: The big idea was that conversations are inherently entertaining and interesting. This one, your listeners will decide whether or not they enjoy.

Paul: Yeah it could get there, we’ll give it time.

Rich: We’ll keep working on it.

Michael: But essentially they’re how we educate and entertain ourselves, and there’s something really interesting in that conversational dynamic, and messaging is how people have conversations today. And so the idea of Talkshow was the tagline, and the idea was texting in public. Where two or three or four of us could have a group messaging conversation where everybody could watch. So the form of Talkshow was a messaging app where every conversation was browsable and viewable. Anyone could start one, you could invite other people to join you, and then you could share them either through the app or on the web. So every conversation not only was obviously like messaging in the mobile application, but also had a permalink on the internet because that’s the way I think about the web, and was shareable out to social media. And they all updated live and in real time.

Paul: So it does one thing but that’s actually, as you’re describing that, that’s a lot of platform. You need a backend that can handle all that data and all the authentication, you need the mobile, you need the web. I mean there’s a lot of front-end work, it’s got to look good.

Michael: Yeah.

Paul: So this is a lot of work.

Michael: Yeah. That’s what I love about it, actually. Like, this is what I love about building products for the internet, is that on the surface they’re like, on the surface, that’s, uh, if you do it right, like, that looks and feels really simple idea and that’s a simple idea I can get my head around. You know it’s classic iceberg, right? So underneath the surface is all of this stuff that actually makes it possible. But yeah, we built a full realtime messaging backend. We used some stuff from some third parties, used a lot of Amazon, and we built an iOS application. I worked with a really, really great iOS developer, Reyner Crosby, who wrote kind of every line of code that people interacted with on the iOS app. Greg built the backend and we had a great web developer and a great designer. So we had a small team of about five of us that were —

Rich: That is the sweet spot, isn’t it? In terms of size?

Michael: I think it is.

Rich: Five person. I can conquer the world with a five-person team. If it’s the right people.

Michael: With a five person team you can do a lot.

Rich: Yeah, yeah.

Michael: You don’t have the coordination tax, and communication tax.

Rich: Exactly.

Michael: That you do with a larger team.

Paul: It’s true everybody’s on one channel.

Michael: Right. Everyone’s on one channel, and you have enough division of labor that you can actually get stuff done.

Rich: Yeah. And it sort of self-selects very very quickly. If person four on that team isn’t running alongside, it materializes in like a minute.

Michael: Yeah you know it really fast. Right.

Paul: So you launch this thing. When did you launch it?

Michael: We…I’ll give you the general timeline. We raised money in last October, so about a year and change ago. We went to beta in January —

Paul: You don’t have to give me the specifics if you’re not comfortable. But like, about how much money does it take? What are you asking people to do?

Michael: I was very lucky. Because as you said, I left Twitter and I had a great network and that was from working in San Francisco for 20-plus years and building a lot of products. Some of them that worked, some of them that didn’t. And was lucky that I had what we thought was a really interesting and compelling idea. We can talk about that in a little bit. And was able to raise a very healthy seed round for an idea and a prototype. And so, you know, on the order of a couple million bucks.

Paul: Mmmm hmmm.

Michael: So we did that in, like, October based on a prototype; we went to beta with a couple of hundred people, kind of January or February; we launched in the app store on April 26th of 2016. And then we…it took us about six months. It took us less. It took us about five months to realize, and then another month to make the decision to actually, that it wasn’t going to work. And so then we shut it down, announced that it would shut down on November 1st and took it out of the store. And then we just closed the service on December 1st.

Rich: Just real quick, Paul, that’s very recent. That’s five days ago.

Michael: Yeah! It’s true. It is. Yeah we just, we turned off the service completely on December 1st.

Rich: So is it, real quick Michael, I’ve never been in this situation. Do you send the investors like an Edible Bouquet? [laughter]

Michael: I’ll just walk you through the history of it. Because it’s not, it’s a pretty short history. We launched, we had some great initial buzz.

Rich: Mmmm hmmm.

Michael: We had fantastic support from Apple, featured us, which drove a lot of downloads of the app and a lot of people that were giving it a shot. We had some really interesting and fantastic people that were hosting talkshows that I enjoyed reading and following along with and engaging with. And we shipped three or four kind of big revisions to the app in the six months that we were in the store, which I’m super proud of the team and the work that we did.

Rich: So all the right things were happening. For those that don’t know, you can’t request to be featured.

Michael: No.

Rich: Like Apple just has to…it’s pretty much an editorial process. They have to pick you out and —

Paul: Not only that, I mean, it was solid working code, built by a good team, it was iterating, it was responding to feedback. I remember as it was coming out it had good, clear notes, and there was stuff happening.

Rich: So all the things you wanted to have happen for a launch, happened, to a large extent.

Michael: Right.

Rich: And you guys executed. I mean, we’re going to talk in a minute about what happened and how it was received, but you guys shipped.

Michael: Yeah, we shipped.

Rich: Let’s not just gloss over that. Right? You guys shipped a full scale, ready-to-grow platform.

Michael: Yeah. We shipped. And what I loved about what we built, and what I love about the team that I work with and that we’re still working together, is we shipped and we shipped well, and we shipped frequently, and I think we shipped thoughtfully. And really, what it comes down to, like, I mean there’s a whole bunch of stuff that we built that consumers never saw, around reporting and monitoring and content moderation and all of those tools, that we spent a bunch of time, you know, building in order to be able to manage a service like this. And that’s in addition to all the things that were on the kind of leading edge of the iceberg. And I think, so what it comes down to is that we realized, in talking with a bunch of users and actually having the product in market, that really it came down to: the concept was flawed. And that’s, you know, 100% on me.

What was wrong about the concept was getting people to do simultaneously has a very, very high coordination cost. So you guys record a podcast every week, and you have someone that actually helps you manage that, right? So we had to schedule this, we put it on a calendar, we had to set up the Skype call, you guys have recording stuff, like all of the, you know, Rich there are cables on the desk that are bugging you.

Rich: Right.

Michael: There’s stuff that have to happen to make this happen. And that cost, that coordination cost, was too high for Talkshow, for the payoff. And so here’s the second problem: so if you can’t get people to do things simultaneously, it’s very difficult to get people to tune in and watch the conversation simultaneously. Which means they’re not doing that, then there’s no opportunity to give your Talkshow host, the people who are actually chatting, realtime feedback. So there’s no feedback loop, there’s no dopamine hit of actually participating.

And then it’s like well, if you did it and you just, you know if it was asynchronous, then like, well, why would I do this here? And there’s still even less opportunity for the kind of dopamine hit of feedback, and it just became like, well if it’s just a place where we’re just going to have a chat or conversation and then publish it on the web, you could do that in a gazillion different ways. You could do it in Gchat, you could do it in Facebook Messenger and just copy and paste and then go publish it on the web.

Rich: Right.

Michael: There’s no reason to have an app, there’s no reason to have a platform, there’s no reason to have a fault model. There’s just no reason for Talkshow to exist. And so when we kind of came to that realization, it was difficult, and as I kind of characterize it to people, it was intellectually easy but emotionally difficult.

Rich: Sure.

Michael: Because it’s —

Rich: That what I was about to ask you. I mean you’re rattling off all the issues with your child.

Michael: Yeah.

Paul: Not only that, you’ve built it. I mean I know one or two people on your team there. It’s a great team. It’s a warm, affectionate, good team to have together. And so I can imagine that’s a source of stress too.

Michael: Right. Right. So it’s, you know…

Rich: You’re supposed to be in denial for at least a few months, Michael. [laughter] You’re supposed to blame the market, and the timing, and maybe Apple, or…

Michael: Right. Right.

Rich: You’re supposed to look around and see who you can point fingers at, because —

Paul: It’s really only a year later that you write the Medium post —

Rich: Yeah.

Paul: Taking responsibility for what happened.

Rich: And it’s just the most dreadful Medium post too, right? [laughter] It’s dark…

Michael: So I wrote that post. [laughter] I actually wrote that post on a plane and landed and was talking with a friend about it, and she is like one of the most blunt, lovely people I know, and is like, she’s like, “Yeah don’t publish that.” [laughter] She’s like, “For two reasons: one is that a) nobody gives a shit. [laughter] and b) it really, like, they won’t have the context, so, like, who cares? They’re only going to take little bits out of context and not be able to… There’s no good that will come out of it.” Which is, like, such great advice.

Paul: These are problems of immense privilege.

Michael: Yeah. Our blog post about the shutdown was like, “It didn’t work, we’re shutting it down, the team stays intact, we’re working on something new, stay tuned.”

Rich: Oh OK. Oh so you’re working on something new now?

Michael: Oh yeah. So the story is, like I went to, so I went to my investors. Our lead investor is August Capital and the investor is David Hornik, who was also on the board of Six Apart. So I’ve known him for a long time. David is a fantastic human being, like one of my favorite people on the planet. So I go to David and I laid all this out, like here’s why it’s not working and here’s what’s going on. He’s like, “Well you have a few options. You can shut down the company and — ” Because we were not burning very much money and we have a whole bunch of money left in the bank. So he’s like “You could shut down the company and return the money to the investors.”

Rich: OK.

Michael: “And then go get a job, and the team go gets jobs somewhere. You could go try and sell the team. I’m sure there’s someone that would love to pick you guys up as an acquihire thing and then you’d go and basically get a job. You could keep working on Talkshow, no one would fault you, but it sounds like from the conversation we just had that there’s flaws and that’s a bummer, because I liked the idea and everyone else liked the idea that invested. Or you guys could go try and build something new.”

Rich: OK so tell me about this food truck that you’re going to be launching. [laughter]

Paul: Well wait, let me say one thing —

Michael: We really like tacos. So we’re really into… [laughter]

Paul: Let me say one thing here too. Michael came and saw me, I think, like, a couple years ago, as he was forming the idea for Talkshow.

Rich: Uh huh.

Paul: And I had a little office at the School of Visual Arts at the time and he sat down and I was being really thoughtful and he was really into this idea and he pitched it to me. And, I mean, when you look at what’s happened, I had no — I was like, that’s a great idea. Go do that. It totally made sense to me. He’s, you know —

Rich: So you weren’t just being nice.

Paul: No! I was like, oh yeah totally, go, like, sure.

Rich: It makes sense.

Paul: I can totally see that. And he had a good model, he thought it all through. Like, this thing was buttoned up and it looked good, and it made sense. And it was only until it got into the market that, you know, suddenly, suddenly these flaws and these issues became apparent. But as we thought it through in that room, it was fine. It would look good. I thought it was going to be great. I was a little jealous. I’m like, “Huh, Sippey’s gonna take, he’s gonna like have a little thing going. I don’t have a thing going.” I was like, maybe I should get in on this Talkshow but I don’t have any money. I remember that very specifically, because he was on a path and I felt a little left behind, and also really believed in the concept. So it’s very easy to play these back but in the moment, and as this went along, this includes me, I was like, “Cool. That seems great. You should totally do that.”

Rich: Yeah. I got to give you credit for, um…most will live in denial. Many people who’ve invested so much in a plan where the world doesn’t seem to be agreeing with it, just keep going and just keep at it because it’s just, they’re too tied up in it.

Paul: I got to tell you though, I would trust this guy with my money, having just heard how he told me about what happened and what went wrong and shutting it down while there was still money in the bank, and running it frugally.

Rich: Well I mean, we’re on the other side of it. I got to imagine there must have been some tough days here, Michael, as you were thinking about what to do with this.

Michael: Oh there were definitely some, yeah, very tough days.

Rich: Right.

Michael: There were very tough days. And very, you know, it’s intellectually easy and emotionally difficult.

Rich: Right.

Michael: That doesn’t make it easy all the way around.

Rich: Right.

Michael: It’s that, you know, God what does this mean for the team? Are people going to want to, like, how are we going to run this thing? We got to build a new product. How are my investors going to react? You get the ego stuff of personal reputation and etc. etc.

Rich: Sure.

Michael: I’ll say this because I’m not, I, people usually don’t talk about this stuff, but for most of the year, I’ve been seeing a therapist. So it’s, like, having actually someone that’s totally, completely not invested, and in fact like you pay to actually listen to you, like, couldn’t be less invested in your life actually be the person that is giving you, helping you think through stuff has been incredibly helpful for me. So that’s, like, I feel again, completely lucky to have been able to do that.

Rich: To do that.

Michael: Yeah but that’s the thing that for me has been, it’s been helpful for me to get through the kind of emotionally difficult part of it.

Rich: Right.

Michael: And realize that it’s the things that actually matter, which are building things that you’re proud of and making decisions that you are proud of, and working with good people. So that’s, those are the things that are the priorities.

Paul: I mean it’s incredibly smart to get that external reference, especially because we’re, you’re in the absolute bleeding heart of this particular industry. You couldn’t sit any close to the beating heart. I guess maybe if you went and sat at Facebook you could. But like.

Michael: Yeah. I think that’s actually, yeah, which is, you know, we have friends that are there.

Paul: Exactly. And just having a human being who is, like, I don’t particularly care how many downloads you got. I care that your relationships with other human beings are meaningful, that that’s longer-term going to be more important. And giving that person a couple hundred bucks to say that is totally worth it.

Michael: Totally worth it. Totally worth it.

Paul: All founders should get therapists. That’s a new part of Y Combinator that I would like to propose. [laughter]

Rich: There’s an arm of Y Combinator.

Michael: I think that’s actually a really good — I think that’s actually a really great idea. I think that they probably should. I think all people should.

Paul: Well if we could turn it into a chatbot, it might be able to get some interest.

Rich: Mmmmm.

Michael: That’s true. That’s right. Just put it on Facebook Messenger and… [laughter] And they know everything out there and all of the rest anyway, so, might as well just tell them everything.

Paul: So are you in [almost a Christopher Nolan Batman voice] stealth mode, or can you tell us —

Michael: Yeah. Actually we’re totally in stealth mode. I will, like, I apologize for being in that mode because it’s just, it’s super annoying and it’s just generally not how I roll. I’m a pretty, having been a blogger for a long time, I’m pretty reasonably open. Yeah we’re working on something that we’re really excited about. I don’t know what form the product’s going to take yet. One of the things that, you know, I’m always trying to remind myself, especially after the last go around, is coming back to those three questions of what problem are we solving, who are we solving it for, and how are we going to measure success. We know, generally, the space that we’re going after. We’re starting to learn more about who we’re solving problems for, and what types of problems they have. So I’m in kind of deep user-research mode, and at the same time we’re exploring some technology stuff. So we’re kind of half, we’re like building and researching at the same time.

Paul: That’s great. I mean look we wish you every bit of luck. When it’s ready, come back and talk to us.

Michael: Yeah, definitely will. It’d be fun.

Paul: We’ll give you a big —

Rich: Shout out.

Paul: Huge plug! [laughter] First of all I just want to say that I really appreciate that kind of transparency, and it’s, there’s a maturity that is the kind of precedent for this, where you were able to separate the intellectual and the emotional, which I think is, surprisingly for the technology industry which prides itself on its logic, is unbelievably rare.

Rich: Yeah.

Paul: People think they are not being ruled by emotion, but oh my God are they. And, you know talking to you, you had a very, very clear reason for why you did what you did to build it, and also why it was the right time to do something else. So that is just very impressive. I’m glad that, it was cool to hear it.

Michael: Thank you.

Rich: It’s hard to undo that. I mean, a lot of founders, even the ones that become successful are, start off with, there needs to be a certain level of delusion. Because everything can be talked — you can be talked out of everything, right?

Michael: Oh, it’s so easy.

Rich: Right.

Michael: This is the thing. It’s so easy to get talked out of, it’s so easy to get talked out of anything. It’s so easy to talk yourself out of anything.

Rich: Of course. So you have to…

Michael: You have to believe. You just have to believe.

Rich: Exactly.

Michael: That’s the thing that gets you up in the morning. Otherwise you’re just stuck.

Rich: Right.

Michael: And here’s the other thing, which is that, like, you’re never going to have perfect information.

Rich: Yup.

Michael: So you know, fine, like, we can go do a bunch of user research and interviews and stuff about this thing we’re looking at. And then it turns out like, well, at some point we’re just going to have a whole bunch of gray. And at some point you have to have faith in the idea of what you’re going to go solve.

Rich: Right.

Michael: To go build. To just go do it. To just, like, go, you know, open up Atom and go edit some code and push stuff and…

Rich: And try.

Michael: Like that’s what has to happen.

Rich: Yep.

Paul: There’s actually very little barrier to doing it, except in people’s heads.

Michael: Right.

Paul: So, Michael, this was great. This was exactly what I hope for, because it’s just good to hear what’s really happening and how people truly do their jobs. One thing we like to ask people to do is tell the audience how to get in touch with them. What’s the, if somebody wants to read something by you or talk to you, what’s the right way to do it?

Michael: All right so if you want to talk to me, my email address is msippey, m-s-i-p-p-e-y, @ Feel free to email. I’m @sippey on Twitter. DMs are open, if you want to DM me that way. And best way to read is, I mean there’s just stuff sprinkled all over the internet by now, so you can Google stuff. Oh and I’ll plug one thing which is, because it’s 2016, almost 2017, I’m really kind of trying to get ahead of the curve and I have a TinyLetter. So you can subscribe at There are no archives, because otherwise it would just be a blog.

Paul: We will include a link to your TinyLetter at the bottom of our Medium post about this podcast —

Michael: What.

Rich: Wow.

Paul: That we’ll distribute on iTunes.

Rich: Huge. Huge

Michael: I, I love — see the internet, right? That the way it works?

Rich: It’s coming together.

Michael: So cool. [laughter]

Paul: Just platforms, hugging each other. Well Michael, thank you so much.

Rich: Thanks Michael, this was great.

Michael: Yeah super fun. Thanks, guys.

Paul: All right come see us when you’re in New York.

Michael: Yes sir, I will.

Paul: All right. That Michael Sippey had some pretty smart things to say about the internet, Rich.

Rich: Well it was a refreshing conversation. A frank, open conversation. Because most things fail.

Paul: I mean, this is the thing: you don’t hear that story very often, but 95% of the time, that’s the story.

Rich: Well if you, oftentimes when you talk to that founder, they’ll tell you about how all the environmental things, externally, the externalities that caused it to fail, you know? They rationalize it, oftentimes.

Paul: You can see though, why someone’s going to trust that guy with a couple million dollars.

Rich: Yeah.

Paul: Yeah. He’s going to tell you what he’s going to do with it, and when it stops working, he went right away and was like “Hey, I don’t think this is working.”

Rich: Yeah. He’s very candid, very open. Which is I think a big part of why people get behind him and trust him.

Paul: Just relationships and trust are kind of it, so.

Rich: Yeah.

Paul: So thank you to Michael Sippey for being on Track Changes. Rich, what if I wanted to get in touch with Postlight?

Rich: You can email us.

Paul: Oh, what would I do?

Rich: We love —


Rich: In fact we’ve got some upcoming podcasts that are just around the contact email, some pretty great ones.

Paul: We really do. We’ve been getting some great email lately and there’s a lot to say.

Rich: There’s a lot to say. And if you want to talk about your projects or whatever you’re thinking about in terms of digital products, we’re open. It’s an open door.

Paul: Yeah. I definitely want to take that moment to remind people that we are a business that, we succeed when we are able to build things for our clients, and we love to hear from people who want to build big, complicated things, and the way that we work with you, is we just give you free advice. And then we decide if the conversation should continue. So it’s low stress. Anything you need, you just get in touch.

Rich: Paul, last I checked, and I look away these days, we were still at five stars. I don’t know what it is today, but I’m going to assume it’s still at five stars.

Paul: Look I respect the opinion of the internet audience.

Rich: There’s only one way to keep it at five stars.

Paul: I do. And I really want people to go, personally, I would take it as a personal favor, if the listeners would go to iTunes and they would review us, and they would give us a star rating of five or greater.

Rich: That’s the only way this can work.

Paul: I really think that it’s in everyone’s best interest, and it’s the way we’ll all move forward as a community.

Rich: Well said.

Paul: This has been Track Changes.

Rich: I’m Rich Ziade.

Paul: I’m Paul Ford., we’re here to help you.

Rich: Have a great week.

Paul: Bye Rich.

Rich: Bye Paul.