This founder’s tweetstorm got my attention (and it’s one that every founder should read)

Joining me is a Mixergy listener whom I’ve known a bit about over the years. Recently, he put out this tweetstorm that really moved me and anyone who runs a company should be exposed to them.

I’ll read a few excerpts in this interview and ask him about what led up to writing them. Matt Mireless is the founder of several companies but most recently he is the founder of Stealth AI, which helps people understand, communicate and be present with each other.

Matt Mireles

Matt Mireles

Stealth AI

Matt Mireles is the founder of Stealth AI, which helps people understand, communicate and be present with each other.


Full Interview Transcript

Andrew: Hey there, freedom fighters. My name is Andrew Warner. I’m the founder of Mixergy where I interview entrepreneurs about how they built their businesses and where, truthfully, I sometimes go home wondering “Am I misleading people?” like making it seem like entrepreneurship is too easy by bringing people on who made it big and they’re going to talk about how they did it.

Joining me is somebody who would listen to my interviews, who I’ve kind of known a little bit over the years and definitely followed remotely. And then out of nowhere, he puts out this tweetstorm, I guess we’re still calling it, a tweetstorm. It’s a collection of tweets that really moved me and anyone who runs a company should be exposed to them.

I’m going to read a few excerpts. He says, “When my second company, the one that I never talked about failed, I walked away with about $100,000 of credit card debt, severe depression. I drove for Lyft to make my credit card minimum payments. My confidence was wrecked. And my son was two years old at the time.”

He eventually got an interview with one VC firm and he talks about how that didn’t go the way that he expected because he says, I’m going to continue reading from the tweets, “Because I wasn’t an engineer, I couldn’t even get a product manager, PM, interviews at companies where I knew the founders. It didn’t help that I was depressed AF and my confidence was shattered. Only one place offered me a job, marketing manager, pay of $70,000 a year.”

He went on to talk about how $70,000 a year in San Francisco, you can’t get anywhere with that especially if you’ve got kids and you got to put them through daycare. And then he talks about this plan that he hatched which culminates in him taking on a little bit more debt and then declaring bankruptcy and getting a job. And he goes on to say, “I remember the day in July 2015 when I called my dad to tell him the plan.”

I’ll pick up the interview from there, but first I’ll tell you, his name is Matt Mireles. I first met him when he was creating this company called SpeakerText. What they . . . They talked to me about using it for Mixergy. It would take the video interviews that I was publishing on the site at the time, auto-transcribe them, and then make the transcript kind of scroll as the conversation on the screen scrolled, and if you tapped on the right word . . . if you tapped on a word within the transcript, you’d go to that section of the video. It was pretty well done. And then he started a couple of other companies that I hope to talk about including the one that he said he wasn’t going to mention in the . . . Oh, that he didn’t mention in the tweetstorm and the one that happened afterwards.

This interview is sponsored by two phenomenal companies. The first if you’re looking to hire developers, I’m going to tell you in a bit about why you should be talking to Toptal. And the second, if you’ve got a team of people and they’re working on Mac computers, if you give them Setapp, you’re going to give them better productivity. But first, Matt, good to have you here.

Matt: It’s good to be here, man. It’s been a long time since we first met, like, I don’t know, a decade ago.

Andrew: Yeah. I want to talk a little bit about that, but first, tell me about what happened. What did you tell your dad? What was this plan? And what did you feel? Be as open as you can here about you talking to your dad.

Matt: Just for some context, one of my resolutions for 2019 was just to be myself and to be more honest and vulnerable. And part of that was talking about some of this dark chapter in my life. Look, I’m in a really good place right now, so, frankly, I can talk about this stuff. But I remember I’d graduated college in 2008. The financial crisis was hit months after. And I had this idea that I was going to become an internet entrepreneur and I had no idea what I was doing. I was completely unqualified, but like, what other option? What else was there? Sure, go for it. And I was really lucky. I also hustled a lot. I ended up in 2010 moving to San Francisco, building a team, meeting some amazing people, you know, raising a bunch of money from . . . I mean, at the time, it was a lot, you know, $1.1 million from Google Ventures and some big names. And it was for a company called SpeakerText and it ended up . . . We sold the company, which sounds better than it was. It kind of started fell apart.

And in 2012, I had a son and wasn’t really planned. I’m very active in his life now. And I just dropped him off at school. He’s with me half time. But his mom and I were just very casually dating and I was a founder and she got pregnant on the third date. And suddenly, I had this company that was kind of falling apart as I had a newborn. And we sold the company in August 2012 and I took two weeks off and started another company.

And over the next two years, we tried a bunch of different things. So it was very early in the on-demand delivery space. We launched something called Swig, which was the first on-demand booze delivery service that evolved into something called EasyFridge which was a weekly grocery delivery service. And I end up competing with Instacart. And I ended up living in San Francisco and SoMa on Second Avenue and Folsom. And I basically took what little I’d earned from the first acquisition and self-financed the second company for reasons we can talk about. And I burned through that cash and started racking up some credit card debt, but having confidence that I’d figured it out, figure it out.

And by early Q2 2014, I was in a lot of debt. And my son’s mother, we were living together. We were together for five years and fighting a lot. And I was trying to fight the startup fight and then fighting at home. She didn’t really ask for the roller coaster that I was taking her on. And I actually ended up living in the same apartment building as Apoorva Mehta, the founder of Instacart who . . . And we knew each other because we’re competitors. And he’d actually placed an order that I’d personally hand-delivered to under a fake name, Johnny Embarcadero, to the Instacart offices. And I showed up on I’m like, “Yeah. I’m looking for Johnny Embarcadero.” Apoorva was like, “Oh, hey.”

We ended up living in the same apartment building. And I ended up shutting that company down. Just I’d run out of steam, was depressed and we ended up seeing this guy basically every day in the morning. And Instacart at the time, they raised 10 million from Sequoia, 40 million from Andreessen, and then $250 million from Kleiner Perkins. And I don’t know if you can imagine having a competitor that just kicked your ass and then finding out that you live in the same apartment building and, like, literally, there was, I don’t know, maybe over 6 weeks, here is 40 million from Andreessen and then 250 million from Kleiner, which, I guess technically made him a billionaire. And there I was, you know, I’d shut down my company, sitting on 100 grand of credit card debt. And it was an insult to injury, I guess I’d say. And just psychologically, it was very painful.

And I tried looking for jobs and I was just a wreck at the time. And I’d gotten an offer, but you mentioned it, like a marketing manager for 70 grand because basically I was paying myself as a founder with none of the upside, but I didn’t believe in the company. And within a year, I basically had given up and I considered myself a failure as an entrepreneur. I just . . . I’d failed. I made peace with it, though. It was kind of comforting. Like, you struggle, you struggle and I was like, I was out of the struggle. And I came up . . . I hatched this plan.

So one of the non-obvious things about U.S. bankruptcy law is that bankruptcy is actually a binary. So it doesn’t matter how much debt you have when you declare bankruptcy. It’s kind of like, you know, a golf club to the nuts. I could give you $5 for it, I can give you 100 grand, I can give you 125, half a million. It doesn’t matter. It’s still the same amount of pain is going to be dealt with you.

And so my plan, and this was before Lambda School or any of these things existed, was to go to Hack Reactor, a coding boot camp, pay with a credit card, and then once the payment went through, I’ll also maybe do some cash advances to pay off my student loans, and then declare bankruptcy. And it wasn’t, like, exciting, but it was a relief.

And I called my dad and I was in tears and I told him that I’d failed, that I was a failure as an entrepreneur and that I was going to do something else. I was going to move out of the Bay Area, I was going to go to a coding boot camp, and get a job someplace. I was going to reconcile myself to be an employee. It sounds, like, crazy, like, that’s like this terrible thing, but I have an ego and in my mind, I was, still I am, an entrepreneur. I don’t work for other people. And admitting that my dream, that the thing that worked so hard for, I gambled big and I just lost.

Yeah, I call my dad, and he’s pretty old, and said, “Okay, son. Whatever you think. I love you.” And it was an admission of just a failure. It was just capitulation is what it was. It was an emotional capitulation to my situation. And after that call, I felt kind of free. It’s like, they say when you’re drowning, you know, before you die, like, you struggle, you struggle, you panic, and then you have the serenity in the last moments before you die, and it was like that. It was serenity because I knew at least I had a plan and I wasn’t going to struggle anymore. And so that’s what the phone call with my dad was about.

Andrew: And things turned around, but maybe we can go back in time and kind of catch up to how you got here. You think of yourself as an entrepreneur. When I look at your LinkedIn profile, I see a lot of internship and photojournalism and paramedic time. Were you an entrepreneur as a kid? Were you the kind of kid who had little businesses? Were you one in high school? No.

Matt: No. Definitely not.

Andrew: So where did this identity come from? Why did you think that you are such an entrepreneur that you would never even get a job?

Matt: My dad was a community college professor. He was basically a communist. I mean, maybe, like, you know, a step or two. No one in my family was in business. I grew up wanting to be a writer. I had fantasies of being Ernest Hemingway, Jack Kerouac, Jack London, adventure, man of the people, traveling around. And so I went to Berkeley for a semester, dropped out, got a job working in ambulance in South Central LA as an EMT, started fighting forest fires in the summer.

Andrew: All this is a way of understanding the world so you can be a better writer. Is that right?

Matt: Yes, actually.

Andrew: Okay.

Matt: I wanted, like, a . . . You know, did you ever see “Dead Poets Society”? Remember that Robin Williams? And when Robin Williams talks about, like, you know, sucking from the pith of life, that’s what I was trying to do. And I did it and, I mean, it changed me. I worked in Compton in the hood as an EMT and I saw a lot of craziness. And it affected me in very real ways. And it was exciting, but, you know, I’d gone back to Berkeley and dropped out again in 2002 sort of permanently. I knew this just wasn’t the place for me. And I tried to write a book about driving an ambulance in South Central LA, but what I didn’t factor in was that the pay was so low that I have to work about 60 to 70, maybe 80 hours a week just to, like, pay rent. And so there was no book writing that was happening. And so I was like, “Okay. Crap.” And now all my friends were graduating from college, getting real jobs, moving on with their lives. What started off as, like, this cool adventure thing, you know, now I was, like, stuck in, like, a union blue-collar job. The union was weak. There was no promotion potential really.

Andrew: So then how did you discover entrepreneurship? What was the hook that got you dragged into this world?

Matt: Yeah. So I end up becoming a paramedic which is another level of, like, training, and then moved to New York City, and ended up enrolling at Columbia. And so I paid my way through Columbia working as a paramedic in the Bronx and Harlem. And my plan was to be a journalist. I end up winning some awards. Really struggled financially, though. I remember my dad who’s very influential in my life, you know, he said, “Miho, son, what the hell are you doing? Columbia is a rich kid school. You’re not a rich kid. New York is the most expensive city in the world. What are you doing, man? You could go to Berkeley.” But I was strong-headed and I powered through and made it work and that was a whole crazy thing in of itself. I ended up winning some journalism awards working for the New York Times and Newsweek as a freelancer, starting as a writer, then a photographer. And my plan was to go . . .

Andrew: I’m sorry to interrupt, but I want to get into the entrepreneurship part because we do have a lot that I want to ask you about with SpeakerText and Swig.

Matt: Yeah, yeah. Okay. Sorry. So, basically, I saw that world getting eaten by the internet in ’06, ’07, ’08.

Andrew: Got it.

Matt: And I wanted to understand business because I understood they had a business model problem. And so when I graduated in 2008, I went to a mini-MBA for idiots summer program at the Stanford Graduate School of Business that I got, like, a scholarship to. And there I got exposed to all these Silicon Valley people and I remember the CEO of Pandora showed up and told the story of how Pandora had been started by a musician. Pandora was a super-hot company at the time. And I was like, “Shit. If a musician can do it,” I’m like, “I can do this.”

And also the people were crazy and it was, like, adventure and excitement. You can actually make money. And it was very creative too. And it just felt like, “Okay. These are my people.” Like, I’d been searching throughout my 20s and never really finding my niche, and then these were my people. And it was very clear. They were crazy in the same kind of way I was crazy. And that is what inspired me to be an entrepreneur.

Andrew: And so how did you come up with the idea for your first company, SpeakerText?

Matt: Yeah. So I was making short documentaries and I would do these long interviews actually like this. And I would always find really juicy quotes that I wanted to be able to, like, share with somebody. You see the text quote, you click on it and go to that exact moment inside the video. And that was the original spark behind SpeakerText. And so that was the experience I wanted to create for people. And so I created a company to do that.

Now, I had no blithering idea how to build software, how to build a business. I’d never had a white-collar office job, so it took a while to get off the ground, but it turns out in 2008, ’09, ’10, it was an incredible time to start a company because there was just so much talent floating around. I hired one guy who was a senior in college. I didn’t have money to pay him, so I gave them an iPhone and I told them, “This thing is the future of computing. If you work with me, I’ll buy you one of these and I’ll pay your phone bill as long as we work together.” And he ended up . . . His name is Tyler Kieft, an incredibly talented engineer. He now runs a big team at Instagram. I recruited another guy, Matt Swanson out of Carnegie Mellon Robotics Institute. And he was incredibly talented. We moved in together and went for it. Yeah. It was not the most obvious transition, but it was very clear to me that I would just figure out how to make shit happen.

Andrew: And you did get a team, the software did work really well. I remember one of the . . . As somebody who was posting transcripts back even then, I found . . . What was it? Andy, one of the founders of Kickstarter. I forgot his last name.

Matt: Perry Chen.

Andrew: No. Well, this guy Andy had this idea. He said, “Look, if you want to have a transcript made, here’s what you do. You break up your audio into these small five-minute bites, put it on Mechanical Turk and pay people a few cents to transcribe each one of these little bites.” And so I created my own little hacky software to do that and I submitted to Mechanical Turk. And instead of paying, what, $60, $100 per hour, I could pay 20 or less and it was just stunning.

And I didn’t know why the big transcription companies didn’t do any of this or maybe they did and they were still marking things up. But you guys had. You found a way to do the same thing, to automate breaking up all the audio to have it transcribed. You had the software working really well. Truthfully, the reason that I didn’t use it was I still have to pay you guys for it and it didn’t solve a major problem, a big enough problem for my audience. My problem at the time was, how do I get more listeners? And their problem was, how do I listen to it in an easier way? This wasn’t solving that big problem. It was sharing clips of texts that not enough people had, if that makes sense. It was a nice-to-have feature.

Matt: Yeah. There was a lot of problems with that company and that product. I mean, I think . . .

Andrew: What else? Why didn’t it work out?

Matt: Well, I think there were some basics. While we were very technically sophisticated, we lacked certain basic things like accounting. So we would actually lost . . . In retrospect, we lost money on every customer, but we lacked rigorous accounting. So we only counted the cost of paying Mechanical Turk, but Mechanical Turk didn’t really provide good results, so we’d have to then manually go and clean up the work which was completely unaccounted for.

Andrew: Yeah.

Matt: And I think, in the end, the core problem was that we saw ourselves as trying to solve a technology problem. And by virtue of building this very talented, but also very young team out of, like, one of the top computer science partners in the world, we were very excited about solving a technical problem. And I think I was, frankly, kind of a weak CEO in that way that I just kind of went along with that and got swept into the idea of, “Okay. We’re going to solve this AI problem, machine learning problem.” It’s what it ended becoming and really lost sight of the business. And it was one of . . . And I think is very common in startups where you have two people who don’t know each other super well running the company and we were just fundamentally were not aligned internally in the vision. And I think in the end, I wanted to build a consumer product company, but we ended up doing something that just made money because that seemed like it made sense.

Andrew: I wonder what’s the thing that made money. But you know what? Let me take a moment to first talk about my first sponsor and then come back in. Are you on a Mac by the way?

Matt: Yes.

Andrew: There were a bunch of people on my team who were on PCs. I slowly have moved almost every one of them to Mac. And by my team, I mean, the consultants who I work with. And the thing that I’ve discovered is, I do things on Mac that other people don’t. They give me the ability to speed things up, little shortcuts that make things faster. I had this one computer that was slowing down and I was going to throw it out and get another one and then I realized, “Wait a minute. Actually, I could just run CleanMyMac on it,” and it would clean up my Mac and make the whole system go faster and suddenly I didn’t have to buy a new computer just because I installed the software.

And I’ve noticed that I do this stuff, but my team, the people I work with don’t. And so I realized the reason that they don’t do it is because they don’t have the ability to go and experiment. They don’t want to pay money for all the software. They don’t know what to try out. That’s what I like about Setapp. What Setapp does is they’ve got over 100 different apps designed just for Mac. So anyone who’s listening to this ad who doesn’t have a Mac, it’s not for you. But if you do, you have some of the top, I think, almost all the major Mac apps are included in here all at one low price, you give it to your team, they get to install this software, they get to improve their computers, be more productive, get more done for you, you pay for it. If you want to cancel, you can cancel anytime. And I’m going to give you guys, if you’re listening to me, 60 day free trial.

When you go into it, I’m going to recommend a few pieces of software that will help you. One thing that I’ve already mentioned is Clean My Mac, it’ll make your Mac faster and also your team’s Mac faster. I really highly recommend that people do things like, well, if you’re doing any kind of PDF or writing or filling out for me, it’s always for accounting or for legal documents, get PDF Pen. It’s software that will make it easy for you to quickly fill out those PDFs and send it out. If you have a lot of Mac apps running, there’s an app called Bartender. Do you know this, Matt, Bartender?

Matt: I think I used it at some point. Yeah.

Andrew: It’s like . . . You know how on the Mac you get all these different menu, in the top right, you get all these different icons and they’re kind of distracting and they keep you from paying attention to your work. Well, this hides all of that in this little corner. It’s called Bartender because it hides all the garbage in your bar and only brings it up to you when you need it.

There’s something called Cloud Monitor. It monitor . . . It gives . . . Excuse me. Cloud Mounter. It lets you mount like an Amazon Web Service Drive as a regular drive on your computer or your team’s computer so that it’s all up in the cloud. And if they lose their computer, they didn’t lose their data. So many other apps. What else? Canary Mail for doing email faster even the Gmail. Ulysses focused writing.

All right. Listen, if you guys want to try this out for yourself for your team, I’m going to give you 60 days for free. If you’re not happy with it, just cancel, move on. But you will be happy with the productivity that your team has and how well they work together when they sign up for this. So here it is. Just go to

I’m kind of embarrassed, Matt, because I kind of made fun of the fact that they gave me this long URL in the past because I said, “These guys are not prepared to advertise on podcasts.” They like this program. They’re supporting it. So they’re doing and they gave me this long URL. They must have gone in and gotten a shorter, like, domain just to make it easy for people to sign up. And a short domain that’s meant just for this is if you go to, you’ll get 60 days for free. Let me spell that Sixty days of over 100 Mac apps that you’re going to love.

All right. Tell me about why it didn’t work out. What is it about SpeakerText that didn’t work out?

Matt: So the . . . I mean, I think there is a . . . Oh, this is one of those questions where I could, like, tell you 17 . . . I’d say the core reason as I think about it is that we didn’t have . . . we’re fundamentally misaligned as a team, and so it became very difficult for us to execute clearly in one direction. Now, the business was cool. The margins were poor.

Building on top of Mechanical Turk and Amazon as a platform was a huge strategic mistake because the incentive structure of that is you pay people per task and the result is that people just try to do as much work as possible which is, like, they’ll create scripts to, like, hit the Submit button or . . . There’s no relationship. They’re just a number to you. And so the only way to sort of maintain quality would be to not pay people, to punish them, which is like the worst possible way. And we built this very sophisticated machine learning system. And I kind of think of it as like a robot slave driver, you know, to, like, catch them when they were messing up and then punish them.

Andrew: You know what, though, Matt? I feel like that you could have overcome. I get the issues with Mechanical Turk that way. I remember even getting people just submit junk in there thinking they could just pass it and get a few cents for me for that task. I like that you guys were creating all this software to improve it. I think eventually you would have figured out, you know, and hire some people in the Philippines that work directly for you, doesn’t cost much and you get great results from them. The thing, though, that I found was, I don’t think you addressed a deep enough problem that people would have been willing to pay you for 10 times more than you were charging to solve.

Matt: Yeah. So the thing that we should have done is instead of charging media companies and turning them into our customers, we should have been in the business of giving them money and helping them monetize. That I believe. And I remember, you know, very early on the company I had a meeting with an investor named Fred Wilson in Union Square Ventures. And I remember he walked up and said, “This is cool.” And it was on the screen. He’s like, “You should figure out how to put ads in this thing.”

And that ended up being one of the biggest mistakes because we would try to get people to use it, people were like, “This is so cool. I’ll pay you for it, but I’m not going to pay you a lot for it. I’m going to pay you as little as I can because it’s just a cost center. It’s not helping the business in an important way.” And so the business model, the nature of it was we were just trying to . . . it was a low-margin business and there’s no . . . It was very little recurring revenue. People would say, “Oh, I have 100 videos. Transcribe them.” And we say, “Woo-hoo.” And then there’d be a trickle of revenue coming in later. It’s a very lumpy . . . It wasn’t recurring. Our margins were terrible and . . .

Andrew: Here is what I do think. Oh, sorry. One more and then I’ll tell you what I do think you guys did really well. Sorry. So, you were saying lumpy business, margins were terrible and . . .

Matt: And I just don’t think that we’re very customer-centric as an organization.

Andrew: What do you mean?

Matt: That stuff was like, I mean, geez, 8, 9, 10 years ago in the rearview mirror. My big takeaway is really about on a little going-forward basis, is all about aligning the internal mentality of the company with the customer and the business. And we were just starting from the wrong end. We were starting with technology trying to figure out how we could get people to use it or to pay us money for it versus really thinking and empathizing with the customer.

Andrew: Yeah. That’s very self-aware. The thing that I was going to say earlier is, what I noticed that you did really well was you got in front of amazing people. My past guests would contact me to say, “What do you think of SpeakerText and Matt Mireles?” and I’ll go, “How is this guy getting in front of all these people to the point where they now want me to opine about his software?” How did you get in front of Fred Wilson? How did you get in front . . . I don’t want to reveal some of the other names because they didn’t give me permission to. But how did you get in front of all these people?

Matt: Well, so the thing is, you know, when you’re a talented writer, I’ve been freelancing for the New York Times, Newsweek, and you come to engineer land, suddenly, you can really stand out. And I think, you know, Paul Graham really knocked this one out of the park. He was a random entrepreneur who started writing essays and now is one of most famous guys in Silicon Valley. I came in and I started blogging a lot and picking fights with people on the internet.

I had a big . . . I had a mohawk at the time. I had a big fat chip on my shoulder because I just assumed that I was never going to be accepted by the money to insiders. And so I used my talent as a writer to then just make a name for myself and there was less volume of content out there, and so it was easier for any particular person to stand out. And then I would kind of say somewhat ridiculous things on interviews, then people would . . . Those things would kind of go viral on the internet as well. And so I was really good, basically, at, like, PR and marketing. And then I just naturally, you know, had like a hustler mentality. And so I would just always be trying to get the intro, trying to meet with people, and just make things happen.

Andrew: What about this? I was reading the book, “Netflixed” and in it, I highlighted this back then. In preparation for this interview, I went back to look through that book and I was so happy that I highlighted the fact that a Marc Randolph, the actual founder of Netflix, I think he considered you his protégé. And you’re quoted in the book about what his experience was like at the hardest days of creating Netflix back when they were a DVD company. How is he your mentor? How are you his protégé? What’s going on?

Matt: Yes. So there was a time back in 2010 when Facebook didn’t have a spam box and you could just message anybody. And so I remember he started getting some press . . . I think he left Netflix in ’06 and kind of was, like, retired and, like, suddenly started getting press. And then I looked him up and I sent him a cold Facebook message. And I remember inviting him to our office . . . At the time was three of us living together in, like, the cheapest crappiest apartment we could find in downtown Mountain View which was the cheapest place you can live in the Peninsula in Silicon Valley. And he’s like, “I got a board meeting. I’ll come by your office after the board meeting.”

And I remember he shows up, he’s got, like . . . He looks like he’s just got a board meeting. And he shows up and it’s like us and like a bunch of like Hispanic families. And like, apartment . . . I told him Suite 5D and it was apartment 5D and he’s looking around and, “Where the hell am I?” And I’m like, “Marc Randolph.” He’s like, “Yeah.” And like, “Matt Mireles, come on in.” And we were charmers, man. I think my co-founder, like, put a shirt on quickly and we invited him into our living room. He was supposed to stay for 20 minutes. It turned into a two-hour conversation and we ended up meeting up once a week for two hours for the next, I think, two years. And he ended up investing in the next two companies I did after that as well.

Andrew: Let’s then talk about what happened with SpeakerText. You sold it for how much?

Matt: I think all in it was $200,000.

Andrew: And how much of that did you get to keep to use to fund your next business?

Matt: I got about 30 grand as, like, a consulting fee to close the acquisition because we basically had run out of money and there was not . . . Like, I needed money to just . . . Even the process of closing the acquisition took time. And so I was paying myself 60 grand a year at the time, so that was actually like half your salary. That was pretty good, it sort of seemed like at the time.

Andrew: And it wasn’t a great exit, but you said that you used it as a way of puffing your reputation up, right?

Matt: Oh, yeah. No. So the way that that unfolded, I’ll tell you a little story here. So we’re doing SpeakerText, we realized that we had a market size problem in probably early 2011. We realized we had a market size problem. One of our investors, a guy named Jeff Ralston. I think he runs Y Combinator now. But he was an angel investor of ours. And we met with him and he said, “Okay. So how are you guys going to get to $100 million a year in revenue?” And we looked at each other and we’re like, “How do we do that? I have no idea.” And we did the math and realize, like, there was no possible way where that would . . . There’s no feasible universe where that could happen.

And so we pivoted the company and tried to build a virtual assistant that was powered by Mechanical Turk and this AI technology we built to manage. It was called Humanoid. And I remember we had a partner from Sequoia Capital showing up at our office saying they’re going to do this, you know, talking about maybe leading a series A and it was very exciting. And we ramped up our burn. And we launched the product and it was a complete fart. And I realized that we needed to do . . . Actually, what you said, like, have our own dedicated workforce in someplace.

And Mechanical Turk was this huge liability. We couldn’t build a good service for people. But we didn’t have enough money at the time to do any of that and my co-founder and I were fighting like cats and dogs. The investors basically went from saying they’re going to do our series A and all these things to basically went dark. And so they basically left us for dead. And I realized that if on the current path, nothing was going to happen, we’re just going to run out of money or die and I wasn’t willing to let that happen.

And so I created a story where a friend of mine had a company that had run out of money with a bunch of very talented Carnegie Mellon engineers. And I emailed every investor, VC, entrepreneur that I’d ever met, the subject line, “For Sale Ruby on Rails Dev Team.” And I remember I emailed Ben Horowitz of Andreessen Horowitz. And seven minutes later, he responded and introduced me to Tristan Walker who was running BD at Foursquare at the time, and went from having no options to having . . . I think we had ended up with five different offers.

And so, yeah, it was kind of crazy. None of the offers were particularly good. A lot of them were companies that none of the engineers wanted to work at. And going through that process was completely demoralizing. So, in the end, we ended up selling the technology to a competitor called CloudFactory that was doing something very similar. They had their own workforce, but they didn’t have this technology that we built to manage their workers at scale, and so they bought it, integrated it, and a deal closed in August 12th, 2012.

Andrew: And you used it as part of your rep, right? This is what you were talking about earlier that you see in the startup world that entrepreneurs were puffing themselves up and giving everyone else the impression that they’re all making it and maybe we’re the only ones who are not because we’re looking from the outside at just all these exits and successes that are not real huge successes.

Matt: Yeah. Because the thing is, is that there’s no upside in being transparent and saying, like, “I’m losing.” Right? Everyone is trying to find . . . No one knows who the next Mark Zuckerberg is. No one knows who’s going to build the next big thing. But everyone wants to signal that they’re going to be the next big thing, that they’re a winner. And you don’t want the stench of failure on you. So what you do is you try to make your failures look like success. And I think the most sophisticated entrepreneurs and investors like, “Okay. Yeah. Sold the company. It was probably pretty crappy.” But most people who are not that sophisticated look and say, “Oh, you sold the company. Oh, wow. You must be really good. You must be really smart. You must be a rich guy,” which is definitely not the truth, but it was very convenient . . . It wasn’t a lie, but it was definitely misleading.

Andrew: It does sound better than saying, “And I had to close it down because it went bankrupt.”

Matt: Yeah.

Andrew: Even closed it without saying, “I closed a sale for zero dollars.” it still sounds better.

Matt: Yeah, I sold the company. I sold the company. And that sounds really good. Much better at a cocktail party than the alternative.

Andrew: All right. Let me talk about my second sponsor. Second sponsor, speaking of hiring, is a company called Toptal. I’ve got to tell you that I’ve been hearing about this guy, Ted Blosser. I’ve got notes now. I’m actually trying to get a little more professional the way that I do ad reads, so I’m going to test. Matt, you tell me as a guy who’s who knows how to sell. Tell me if this comes across as too much of me reading. But I sat last night with my wife at the dinner table and I said, “I’ll write out my ad instead of just, like, winging it and sometimes crapping it out.”

So Ted Blosser is a guy that I read about, so I wrote notes about him. He realized that companies need to train their employees and these businesses are actually willing to pay for software that’s going to help them train their employees. So he created a company called WorkRamp. And if you look around, you’re going to see the corporate software especially for training is kind of crappy, it feels a little bit like you’re going back to the old Microsoft DOS days because it’s corporate enterprise software. Ted decided that what he wanted to do is create something better. So he talked to Toptal and he asked them to find a developer for . . . Excuse me, a designer for him who could create learning software that enterprise employees would actually want to use.
He wanted a designer who had consumer experience, you know, like when you’re using consumer software, it’s fun, you’re almost despite yourself chatting on it, despite yourself sharing on it. So he wanted that kind of usefulness and fun engagement, but he also wanted a designer who worked in enterprise and understood that big companies need things like good admin panels.

And so they hooked them up with a designer named Benoît Chabert, I hope I’m pronouncing his last name right, who was just going to give the company some outside guidance and show them how to build things. With Toptal, yes, you can hire developers, yes, you can hire designers. You could do it full time. You could get them part-time. But you can also just get consulting services the way that Benoît was looking for. So they hired this guy, he started work . . . Excuse me. The way that Ted Blosser was looking and he found Benoît was the designer. It already feels a little bit too much like I’m reading, doesn’t it, Matt? I’m losing myself in the words. I think I might be better winging it. What do you think?

Matt: I say wing it. Although this is not the first time I’ve actually had into the wild, a friend of mine recommend designer from Toptal, or to use Toptal to find designers. So, for what it’s worth.

Andrew: All right. How about this? I’m going to put the notes aside and I’m just going to tell you the story as I remember it instead of trying to read it, instead of trying to be overly professional. What they ended up doing with this guy, Benoît was putting him into the company, giving him access to their Trello boards, giving them access to their Slack, getting him on Zoom, the guy started getting so much feedback. He was such an engaged part of the company that they said, “You know, can you actually just design this for us?”

He revamped the whole thing with them for WorkRamp and . . . Let me get this right here. I’m going to actually read this part so I don’t get it wrong. After implementing the new design, sales for WorkRamp increased dramatically by bringing in new clients like Vidyard, Fivestars, and Optimizely, WorkRamp fueled their growth and got more than $2 million in new funding from Slack, Y Combinator, Reddit founder, Alexis Ohanian, and others.

So I’m going to close it out by saying, if you’re out there and you want to hire a designer, if it’s for consulting services, if it’s full-time, part-time, just like you can hire developers from Toptal, you can hire the best of the best. If you’re curious, go to this page I’m about to give you, hit the button, and you can get on a conversation with somebody at Toptal who can give you some feedback, some guidance and help you understand what’s possible for hiring through Toptal.

Here’s a URL where, of course, when you use it, you still get the 80 hours of Toptal developer credit when you pay for your first 80 hours in addition to a no-risk trial period. So here it is. It’s Top as in top of your head, tal as in talent,,
All right. I’m going to do a little evaluation. This is the part where I don’t think I should be evaluating in public, but I can’t help it. I think what I should be doing, number one, I do think it’s better for me to have done my homework and written out a case study about them. I should have instead of reading the whole thing, this is what I’ll try next time, just write a set of bullet points on what I want to say with the names that are important and just tell the story but have the bullet points that remind me of what’s important to say. What do you think of that?

Matt: I think it’s a good idea. A good idea.

Andrew: But I do like this whole WorkRamp story. These guys did really well. The design looks hot. All right. You close it out. How did you come up with the idea for the next business, Swig?

Matt: So it was actually an idea that I had wanted to build in sort of the dying days of SpeakerText was, you know, Uber . . . You got to understand the time. This is 2011, 2012, Uber was very brand new. The idea that you hit a button and, like, stuff would come to you was a new concept. And I originally had this idea for one-tap beer and pizza. You hit a button and beer and pizza. And that was the original idea and I ended up, like, evolving or simplifying into, like, “Okay. What if you hit a button and you just get a beer delivered to you?” And so that was Swig, on-demand booze delivery.

And one of the things, a mistake, frankly, that I made is that I tried to self-finance it. I basically I’d seen how my mentality had changed after we’d raised money in SpeakerText. I went from being this sort of like swashbuckling hustler to trying to like be a CEO, whatever that meant. And all the things that had kind of gotten me to where I was, I sort of like jettison them and tried to become something I wasn’t. And so I blamed that on having raised money, and so I instead said, “Okay. I’m not going to raise money until we have product market fit, until I really believe because once money creates this pressure.” And so I self-financed it, which first couple of months, not a big deal. And it started working, but then actually having to, like, hire people to do deliveries and it was really lumpy. People order stuff at 1:00 in the morning. It was cool experience, but in terms of a business, you know, the economics were not very good.

And within four or five months, we were split. We had consumers ordering and those were, like, money losers, basically. They’d order, like, you know, tiny bit 1:00 in the morning and then we had startups who were saying, “Hey, I don’t need this right now. Next Thursday, could you bring us $200 worth of beer?” And I was like, “Oh, okay. It doesn’t have to be . . . I don’t have to run around 1:00 in the morning. This is good.” And then they loved it and pretty soon we’d have these office managers say, “Hey, actually, look, I really don’t know anything about beer. Could you just, like, buy us $200 worth of beer? I’m not . . .

Andrew: Makes sense.

Matt: . . . even going to order it.” And it was like a weekly delivery and then we could sort of like run like a milk truck route, so the logistics were much easier.

And I was doing this and at the same time, you know, I had a young son and my son was like one years old at the time, and we were spending a ton of money on groceries and we’d come home to an empty fridge and then I ended up ordering out and spend this money on food delivery. And what I realized is that even I would . . . When I would buy beer, I’d always buy it with my groceries. And what I realized, that’s how most consumers were doing it.

I said, “What if we could take the same model? If you have someone that you just outsource the entire grocery shopping experience for you, say, here’s my budget, here’s how many meals I need and just bring me stuff that I want,” which is also nice because we had no real-time inventory of what was in different grocery stores. And so we turned this lack of real-time inventory into a feature and we pivoted the whole business became something called EasyFridge. Never come home to an empty fridge. And every week you’d have a personal shopper, manage your budget and buy groceries for you. And, frankly, it was an awesome service. People loved it and they would tell us about how they were saving literally hundreds of dollars a month because they were no longer spending money on takeout or food delivery and they were just cooking more food at home and living health.

Andrew: But what about this, though? I don’t know what I need from week to week. There are handful of staples, maybe 80% of staples, but the other 20% change so much that you couldn’t anticipate it, and with the other unanticipated 20%, the 80% that is consistent is meaningless.

Matt: Yeah.

Andrew: Kind of weird that way.

Matt: What we did is that basically we would target stay at home moms who were looking to re-enter the workforce and who had, like, some part-time capacity and knew how to shop for home. And so you would have a dedicated shopper who was literally like, “Okay. Tell me what you like,” and then we’ll just literally pick everything for you.

Andrew: Got it. Okay. That makes sense.

Matt: Imagine you’re someone who just literally bought you stuff and came up with ideas for you. And so you just didn’t have to think about it at all.

Andrew: Right. So they might say, “I see that you like peanut butter and you like sun butter. Did you know there’s also almond butter? I picked some up for you,” and I’d be okay with that guy. Got it.

Matt: Yeah. Or they’d be like, “Hey, actually, I just saw that this is on sale, so I got you a really great deal on . . . ”

Andrew: Okay. It’s like having your wife. All right. Why didn’t it work then? You talked about Instacart raising a lot of money, so obviously you were competing with someone who’s flooded with money. Why else didn’t it work?

Matt: Honestly, it was the two things. We didn’t have the team, but honestly, it was my . . . At the same time, I was trying to make this work, I was going deeper into debt and really, my home life was not stable and just fighting all the time. I was getting depressed. I had a co-founder but he wasn’t . . . He’s a nice guy but wasn’t really committed. And I didn’t believe in myself.

I basically, I went out to raise money and actually Marc Randolph cut us a check for 10 grand. I remember doing this little happy dance. And then 24 hours later, I just felt this dread because I knew if I took his money . . . Because we had a relationship. Some people they’ll raise money from investors and whatever, they’ll shut the company down, they don’t care. But, like, if you give me money it’s because I believe that I can turn it into more money. No guarantees, but I believe it. And I didn’t believe that about myself. I didn’t believe I could do it. It was like I was on a roller coaster. I wouldn’t want to be on the roller coaster anymore.

And I called him up and I said, “Marc, I can’t take your money in good faith. I don’t even believe in myself. And I care about our relationship.” And so I decided to give him the money back, 100 cents on the dollars and then shut the company down. And it was really just I was exhausted and really depressed. I couldn’t do it.

Andrew: All right. I get that. And that brings us back to where we started in the interview. You did mention the beginning of the interview that things have turned around for you. And I’ve got a checklist item here to make sure that I come back and explain that. It’s because of a conversation you had with who in the garage that you’re recording this interview from?

Matt: Yeah. So, after that, after we shut the company down, I never tried to look for a job before and VC is kind of one of those things that, well, if you’re an entrepreneur, VC seems like the next obvious choice. So I pinged a guy that I’d known from the New York startup scene named Chris Dixon and he recently joined Andreessen Horowitz as a partner and I said, “Hey, I’m interested. Can I get your advice on going to VC?” He said, “Hey, actually, we’re hiring for our deal team here. You should interview.” And I was like, “Oh, sweet.”

And so I ended up going through a five-month interview process there that was just kind of insane. And I told my friends about it. I was really excited. And one of my friends said, “Hey, another friend of mine is actually interviewing for the same job.” So I met this woman named Linda Pouliot. And she’d started a company called Neato Robotics that I’d heard about because they’d done some crazy AI. They were like, basically, the first consumer product to ship the technology that is in, like, self-driving cars, essentially.

And so we had lunch, and she wanted to start a robotics company. We’re both not really feeling the Andreessen job, but the money sounded really good and the name was awesome. And I pitched her on this idea over lunch. I said, “Oh, how about . . . What if you made, like, dishwashing robots for restaurants? You could, like, sell it as a service. It’s like half the cost of human labor. This is a clear benchmark. It’s very clear where the value is. They’re all just going to move around. You could automate . . . I used to have to do that job. It sucks.”

Andrew: Cleaning dishes.

Matt: And she was kind of, like, blasé about it. What’s that?

Andrew: You used to clean dishes.

Matt: Yeah. When I was in college, I had a job where I had to wash dishes in the back sometimes.

Andrew: And this was just you, you’re sitting down with her and you’re saying, “Hey, you know, it would be cool if somebody created a robot to clean dishes so that people don’t have to do it. It’s kind of repetitive. It’s . . . ”

Matt: For restaurants.

Andrew: For restaurants. Right, right. Right. Got it. So you’re sitting with her, she’s impressive. Neato . . . Isn’t Neato, they make a vacuum cleaner too, one of the robot vacuum?

Matt: Yeah, yeah. It’s a robo. It’s like . . . They’re the number two globally to the Roomba.

Andrew: I switched from Roomba to Neato a while back. I don’t even hit that vacuum anymore, but it is amazing. It is so . . . In my experience, it was better than Roomba. It was that good. All right. So I see here she’s the founder of the company. And so you’re telling her, “Hey, this would be cool.” She comes back to you a little bit later and says, “Hey, you know, this idea that you told me about?” And what did she say?

Matt: Yeah. No. So, literally, I think it was the day after I had this conversation with my dad where I had told him I’d given up. I told him I was going to declare bankruptcy. And she’s like, “Hey, you know that idea . . . ” She texts me. “You know that idea you told me? It’s an awesome idea. Let’s do it as a startup.” I was like, “Oh, hell no. Wrong guy. I’m out of the game.”

Andrew: Why you? Why did she want you?

Matt: Because it was my idea and I think I was the . . .

Andrew: Who cares? Ideas are everywhere. You got no experience doing this. She’s got tons of experience. She’s got a great name.

Matt: That was my immediate reaction too.

Andrew: Yeah. Okay. What did she see in you is what I mean? This is the same question that I asked a lot of people who got into Y Combinator in the early days. What did she see in you?

Matt: I was a good front man. I think she . . . I’m loud and out there and good with press and whatnot and I think she is much less comfortable being in the spotlight. I think she’s much the way . . . She likes managing individual relationships and was never anywhere near as comfortable as me being public and loud and making sort of, like, brash claims.

Andrew: Okay.

Matt: And I think the original idea it was sort of like a hustler builder combo. But I was like, “I’m done. I’m out of the game.” Like one of those mafia, like, crime movies where it’s like, “One last job, Jim.” I was like, “No, I’m done. I’m out. I’ve got a plan. I’m going to declare bankruptcy. I’m going to move on with my life. I’m off the roller coaster.” But she was really insistent, and I was like, “Well, I got the garage. There’s a whiteboard in here. You do the math.”

And we did the math and the economics and the market size and I . . . I’d done a lot of these different exercises. I was like, “Shit. This is actually . . . This could be really big.” I’m like, “Do you think we can build it?” She’s like, “Yeah.” And I was like . . . She’s like, “Yeah, I told you. Let’s do it.” She’s like, “You should be the CEO.” I was like, “No. No, no, no. No. No, no, no. I just literally quit and gave money back. If you’re going to be a founder CEO, you’re going to get, like, kicked in the face for indefinite amount of time. I can’t do it. No. You be the CEO.”

And she was really the one that wanted to do it. I was like, “Well, it’s a cool idea, but I’m not . . . Why me? I’m not . . . I don’t know anything about hardware, about robots. I don’t even have an engineering degree.”

Andrew: What’s the math that got you to feel comfortable with this? The math of building the robot, the math of what?

Matt: The economics of the business and the market side.

Andrew: What were you looking at?

Matt: Okay. How much does a typical restaurant spend on washing dishes? And somewhat per year on the labor component, something between . . . I think the math we did it was something between like 30 to 60 grand a year.

Andrew: Okay.

Matt: Or what if we charge half that. I was like, “Okay. Well, half that, between 15 to 30 grand a year.” And then how many restaurants are there in the United States?

Andrew: Got it.

Matt: And that’s in the hundreds of thousands.

Andrew: And so can we make a device that we could lease out for 15,000 a year that would do the same number of dishes as a restaurant . . .

Matt: Yeah, that just replace labor.

Andrew: [inaudible 00:59:39]. Got it. Okay. And so you’re doing this, you get together with her, the two of you decide you’re going to co-found this company. The split is she gets a bigger split than you, right? You’re the front man, she’s the one . . .

Matt: Yeah.

Andrew: Okay. How much of the business did you get?

Matt: I think we did like 55-45 something like that.

Andrew: Wow. Okay. And you’re the guy, though, who goes and raises money as I understand it, right?

Matt: Well, so we were doing it . . . We did that together. Honestly, I wasn’t totally sold on the whole concept. Do you understand? Mentally I was done. I was like, “Okay. I’ll try this.” And she was the one who was really excited and pushing it and making it happen. And so I was like, “Well, let’s talk to a couple of investors. And you got to understand, my experiences with fundraising before this is you talk to dozens and dozens and dozens of investors. There may be in the end you got one or two yeses and that, like, snowballs into something.”

The first investor we talked to go like, “Yeah, this an idea.” Like, we had a two-page literally written in pencil business plan. “What do you think?” He said, “Don’t talk to anybody else. Come back next Monday and meet my partners.” I’m sitting there looking at Linda like, “What? Has this ever happened to you because this has never happened to me?” And then I’m like, “Oh, don’t talk to anybody. Yeah, sure.” And under the desk I’m sitting there, like, texting somebody like, “Hey.” You know, like, pretending to due diligence on the firm with a competitive firm where I met a guy at a party and that guy says, “Come in at 8:00 a.m. tomorrow.”

Andrew: Because the move is, “Hey, these guys want to give me money. Should I be talking to them about this idea?” that kind of thing as a way of getting the second company to be interested.

Matt: Yeah, like, “What do you think of these guys? Are they legit?”

Andrew: Got it.

Matt: Because they’re talking about. I’m just trying to diligence them. And then he says, “Come in tomorrow morning first thing and meet with us.” And then that turns into the second meeting. So it’s, like, the first one is a Monday, second meeting is a Tuesday, third meeting is on a Wednesday now.

And then we’re waiting, then that kind of starts happening and then the next week I have lunch with a friend of mine named VJ. And we’re going to go in for our final meeting to some other firm, and VJ said, “Oh, Matt, dude, I love this idea. Can I invest?” I’m like, “Ah, dude. Thank you so much. I really appreciate it.” I was like, “That’d be cool.” He’s like, “Would you like the money now?” I’m like, “We don’t have, like, a bank account or a company set up or anything.” He’s like, “No, that’s cool. What are you going to call . . . ” And he whips out a checkbook and writes a check for 10 grand on the spot and he’s like, [inaudible 01:02:32] What did he call it? He called it Bistro Technologies Inc. And he writes us a check and it was like out of a movie. It was crazy.

And within, like, a couple of weeks, we ended up closing I think $600,000 in seed capital. Lemnos Labs had put in half a million bucks and Marc Randolph came in, invested again and one of my other mentors. And suddenly I was back in the game. And I remember when the wire hit from Lemnos and I was driving and I pulled over and I start bawling. I thought I was done. I thought I was out and suddenly I was back in the game. And I’d never had an experience like that before with raising money. It had always been so hard. And it was . . . Yeah, that company turned into a bit of a rocket ship. It turns out that starting a company to make dishwashing robots in 2015 would benefit a lot from, you know, the election of Donald Trump. When you elect a xenophobic nationalist running on an anti-immigration platform, well, guess who washes dishes in restaurants? Immigrant labor.

Andrew: Right. I see.

Matt: And so suddenly, there had already been a labor shortage in California, but now suddenly there was a dramatic labor shortage, and so the market for a dishwashing robot to wash dishes at restaurants that they literally couldn’t hire anybody to do the job got crazy.

Andrew: Wow.

Matt: Yeah.

Andrew: And so you guys raised over $30 million. I saw a video of the robot. All I can confirm, by the way by looking at Crunchbase is $30 million. I’m going to leave it there. I know that you don’t want to get too deep into the funding. I saw a video of this in operation. People just come in and stack their dishes on these little things that you give restaurants, the dishes. It’s only dishes. No cups, no silverware. It’s just the dishes go into machine, takes one dish at a time, squish it with water, spins these bristle things on it to clean it off and then sends it out for someone else to do the . . . No. Then goes into the dishwasher to do the last bit of cleaning, but the hard chunks of food get cleaned out by your robot. That’s where we are right now. And customers are buying it? It’s in restaurants?

Matt: So the way that the business works today is . . . Well, actually, one of the hacks that we realized is that making something you could install on-premise was very expensive and hard. And so we launched actually selling dishwashing as a service.

Andrew: Kind of like linens is what I read, the way that restaurants will have their linens all dirty, they’ll put it in a bag, there’s a company that comes picks it up, gives other clean linen and washes the dirty stuff. So that’s the way it is now, dishes as a service, the customer just load it up. And you do have customers?

Matt: Yeah. I mean, I can’t . . . Yes, definitely. I can’t go into, like, the details there. I left the company a few years ago. And so I’m . . .

Andrew: Did you get to take money off the table in any of these rounds? I see Sinovation Ventures which is the Beijing, China investment company, first-round Baseline Ventures. When they all came in and put money into the business, you get to take any of this money out?

Matt: Yeah. In 2007, a guy named Steve Anderson who runs Baseline he had a leading a series A into the company at . . . I can’t say, but like a very crazy or pretty crazy number on evaluation like many bananas, in my opinion, you know, at least compared to anything else I’ve ever done. And I’d left the company by that point and I was able to sell a $1.5 million worth of stock.

Andrew: A million and a half dollars’ worth of stock.

Matt: Yes.

Andrew: So this guy who at the beginning of the story was calling his dad up to say, “Dad, I’m going bankrupt. Dad, I failed as an entrepreneur,” the very next day has a conversation that leads to $1.5 million in the bank giving him safety to think about the next step. And I know that you’re working on something that’s secret right now. But that’s what happened?

Matt: Yeah.

Andrew: So what am I taking from this? What do I . . . It’s not like at the end of this I could walk away going, “You know what? The thing to do is send out offers to 50 people because that’s what worked for Matt.” No. What am I taking away from this that I could use when I’m worried, when I’m in a similar situation?

Matt: I’d say two things. One, I think before that I tried lots of, like, incremental things. Like, I tried safe ideas. And the safe ideas . . . What seemed safe, they would never break through the noise. And I think one of my big lessons is, you know, when you walk and say, “Dishwashing robots for restaurants,” that turns had no one . . . You haven’t heard 50 of those pitches. And the fact that we’re doing something so crazy and so new made all the difference.

And I also think, like, quite frankly, you know, surface area of opportunity. No one really remembers your losses, your failures other than you. I mean, you will. I do at least. But it’s a numbers game of at-bats, and I think especially if you try things that are really ambitious and you meet people who are awesome and talented and surround yourself with great people, you know, like, literally . . .

Funny story. So one of my friends, it’s a guy named John McClelland, he had moved to Chicago. He was a guy who was like my role model. He had a startup, had a bunch of debt, didn’t work, went to a coding boot camp and got a job. And he was in Chicago and said, “Matt, dude, where you are it’s like the bus leaves every 15 minutes, man. Just be by the bus stop.” And I was like, “Yeah, yeah, maybe for other people.” And then, you know, like, three days later Linda calls me up or texts me.

And so what do you make of this? When you have . . . When opportunity knocks and you know something is a really good idea, go for it. And then quite frankly, when you have an opportunity to sell and, you know, like, it’s there, go for it, especially if you’re not running it, you’re not there. There’s a bit of luck. There’s a lot of hustle and then definitely, like, a bit of luck here.

Andrew: Here is what I took. You might notice I’ve got my Apple Pencil in my hand. I freaking love the iPad. So I’ve been taking notes. Here’s what I got. The number of at-bats I’ve heard a lot, but it seems to keep coming up. Just keep on taking more at-bats in entrepreneurship. Just keep on trying more and more ideas. Obviously, they need to make sense, so it’s not just some random idea that you don’t believe in. And then also that nobody remembers your failures. I don’t know how many other people if I talked about SpeakerText would remember it the way that I do, right? It doesn’t. They don’t remember and they also don’t associate it with the failure, but God, in the moment when it’s not working for you, you feel like you’re a failure and everybody knows it. In reality, it’s a temporary thing and then nobody gives a damn about it now, and they definitely don’t remember later. And those are the two big things that I’ve gotten from it. All right.

Matt: I also think . . .

Andrew: Go ahead.

Matt: The third is do crazy stuff. Be ambitious. Because if we were building just like another SaaS app, some incremental thing, that craziness wouldn’t have happened. And I think being more ambitious because when you’re . . . It’s, like, when you’re . . . You play poker?

Andrew: Yeah, occasionally.

Matt: You know, when you’re playing with the short stack and then you start thinking differently, you start playing not to lose, you stop playing to win. And I think that you have to play to win. And when you’re running low on money, on energy, high on fear, you start playing not to lose. And you’re never going to win when you play not to lose.

Andrew: No. I’ve noticed that when people have short stacks, they take more risks, they go in more and it’s amazing. They think they’re going to go home because we’re playing tournament style and they only have a few chips left, so they push in more often, they go into more pots, and as a result, they come back more bigger . . .

Matt: Exactly.

Andrew: . . . more than you’d expect them to. And it’s the same thing here I get. All right. I get what you’re talking about here. Here’s what I don’t get. How can people connect with you? You did this great interview with me. I feel like people are connecting with what you’re saying. I don’t even know how anyone could stay in touch with you or say thank you for this or any of that.

I just did an interview with this entrepreneur recently, freaking, the number of people who contacted him afterwards through me directly is unreal. And I know people are going to want to connect with you. I don’t have a website. I don’t have a thing to promote.

Matt: Yeah. No.

Andrew: How do they connect with you?

Matt: Yeah. So follow me on Twitter @mattmireles, M-I-R-E-L-E-S, Matt with two Ts, and then my blog. I’m mostly on Twitter these days.

Andrew: That’s where we connected.

Matt: Yeah. And you can subscribe to my blog. And there I think there’s a contact form, you can hit me up and it’ll send an email directly to me. I think those are the best two ways. I mean, like, I run a company now, you know, full-time. I ended up starting a company with one of my . . . I started angel investing after I . . . I’m not writing like huge checks or anything, but I started angel investing after this deal and I started a company with my favorite portfolio founder, a guy named Yousif Astarabadi, who’s freaking awesome.

And so running a company full-time, so I’m very busy doing that. You’ll hear about it. It’s an AI company. It’s definitely in the crazy ambitious universe. So I don’t have tons of time, but, look, I was a random dude, a random hustler once upon a time and now to the extent I can, I try to pay it forward. And that’s why I talk openly about this stuff is because I don’t think that people . . . Like, you hear these stories, if you’re friends with somebody, you know what they went through, but they don’t ever say it publicly. But there’s so many people who don’t have that connection, who don’t know somebody who’s been through this stuff. And I don’t want to be . . . I have friends who’ve been through craziness and been homeless, had nervous breakdowns or whatever, now they’re big names, but they don’t ever talk about it. And I don’t want to be that guy.

Andrew: Thanks for doing the interview. I got it. I’ve got to tell you, so I was doubting whether I should have been so open about my failure with the ad that I did for Toptal. It was rough and it definitely wasn’t great, but I feel that I need to be open like that because people connect more with that. The more these generic sponsors messages that I see now on more and more podcasts, the less I remember the name. It doesn’t feel connected. It doesn’t feel like a real person cared enough to put it out there. I think the same thing here. We don’t want the next guy who tells us that everything worked out. We can read that BS. I feel like if you let people know the hard edges in your life, the problems, the failures, they connect with you more.

All right. Matt, thank you so much for doing this interview. I think that the response to this interview will bear what I set out. I appreciate the two sponsors who made this interview happen. Yes, as I said, Toptal is a sponsor. If you need to hire developers or designers, go to And if you’re on a Mac and your team is on a Mac, you really should be trying out the software. I’m telling you, it’ll make your computer better, it’ll make your people more productive. And frankly, just go and try it 60 days for free when you go to, setapp . . . I wonder why they call themselves Setapp. That’s something I got to find out. And I’m thankful to them for sponsoring. Matt, thanks for being on here.

Matt: Thank you.

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