Boundless Podcast: Pauri Pandian - Tennis as a career, coaching & healthy masculinity (Episode 11)

[01:00] Paul: Welcome to The Boundless Podcast. I'm Paul Millerd and I created this podcast because I'm passionate about making sense of the future of work and having conversations with the innovators, creators, and thought leaders who are carving their path in today's fast-changing world. You can check out the podcast and more on boundlesspod.com. So today I'm talking with Ben Dubot, who's the founder of a startup that is using technology to fight terrorism. But what's more interesting is the path that took him to where he is today. He faced a lot of setbacks, and I think what's interesting is just kind of following his curiosity, how that evolved over the years, how he responded to setbacks, and how he ultimately pursued what he was most passionate about.

I hope you enjoy the podcast today. Again, if you want to find out more information, check it out on boundlesspod.com. If you are interested in supporting my efforts and journey more, you can check out in the show notes my link to Patreon, which lets you support the podcast for a dollar a month or more. And thank you so much again for any of your support. Enjoy the pod today.

[02:26] Guest 2: Ben, thanks so much for joining me today.

[02:29] Ben Dubow: Thanks for having me.

[02:31] Guest 2: Of course. So I'm excited to talk with you today. We've known each other for a while as friends through the same volunteering group, but I've recently heard more of your personal story when you presented on a panel. I think this was last month, entrepreneurship panel, and you were sharing your journey, which is pretty— I thought was pretty fascinating. And you talked about your journey from essentially delivering pizza to now a founder of a company fighting terrorism. So we're definitely going to dig into that, but I'd love to just start back in college.

And you started and majored in Middle Eastern Studies. So when I was starting college, I had no idea what I wanted to do. How did you pick a major like that?

[03:16] Ben Dubow: Yeah, uh, so I actually went into college planning to major in urban studies. SimCity composed an embarrassingly large portion of my free time in high school, and when I took my first urban planning class, I was thrilled to find a bunch of other nerds where the same was true for them. So that was the plan, and I actually did wind up majoring in urban studies as well. Uh, for my foreign language, I wanted to take Hebrew originally, and for my alternate I put Arabic because I thought it was pretty similar. Uh, it's not really, uh, but that was what I thought at the time. I actually didn't get into Hebrew, got into Arabic instead, and was just going to take it to fulfill the requirement.

Then my sophomore year, one of my best friends, my roommate, said that he was going to join the Marines after graduating. Which made me start to think a lot about my duty and my obligation. And if I was gonna know a language as valuable as Arabic, I would have to put it to good use. So I wound up majoring in Arabic and Islamic studies. Wow.

[04:30] Guest 2: So it, it was almost random that you ended up in Arabic only because you couldn't get into, uh, Hebrew, you said it was?

[04:38] Ben Dubow: Yep.

[04:39] Guest 2: So where, where did that take you? So you started thinking about, okay, what is my duty? I'm learning Arabic now. This is kind of my focus. Where, what were you starting to think about after college and beyond?

[04:52] Ben Dubow: Uh, yes, I wasn't completely sure, probably diplomacy or intelligence or something related to foreign policy. I did have an interest, uh, from pretty early on in foreign policy. Uh, started reading The Economist every week at like 19 or so. Uh, so that was the plan. It really wasn't well formed though.

[05:15] Guest 2: Yeah.

[05:15] Ben Dubow: Even junior year, even as late as junior year.

[05:19] Guest 2: So talk to me, so you say diplomacy and intelligence, so I am not an expert in those fields. What does that actually mean? Like what is the type of job you would actually do in those fields?

[05:30] Ben Dubow: Yeah. Uh, I mean, so I could like go through if you want what sort of the career progression actually wound up being.

[05:38] Guest 2: Yeah. So let's dive into the path. So what did you end up doing? I mean, you had a couple of pit stops before you ended up where you are today, but so what did you end up doing right after college?

[05:50] Ben Dubow: Yeah. So, so I could actually start my senior year. I began an internship for a firm, a private firm that mostly worked with news agencies, but also worked with a lot of government agencies where I was monitoring jihadist and white supremacist activity online. And coming from kind of carefree life of senior year of college to this job where every day I was looking at just the absolute worst of humanity, seeing videos of hospitals being bombed, of mutilations, children soldiers, uh, and More than anything, seeing that the more egregious the action being depicted, the more lavish the praise that was heaped upon it really stuck with me, really challenged what I thought I knew about humanity, what I thought I knew about what drove people.

I spent all my free time after that reading every book on psychology, on ethics I could find to try to understand how something that was so repulsive to me could be attractive to somebody else. So I got a full-time job where I had been interning about 6 months after I graduated. I got an offer doing something very similar, but for CIA. And about a year after that, I got an offer from State Department to join the Foreign Service, which is the diplomatic corps. The United States.

[07:29] Guest 2: I'd love to just pick on that in, uh, so in college, you're a senior in college and you're getting really deep into this and it sounds like you have a pretty profound experience seeing all these things. How were you relating to, I mean, just your classmates at that point? That must've been pretty intense. And I mean, I know I was not having those experiences as a senior in college, but, um, how did that kind of change how you're seeing things?

[07:55] Ben Dubow: Yeah, I mean, I really didn't talk about it much, you know, like you come into a place like that and the first thing they say is this doesn't go on your resume unless you're applying to people who would know who we are already. Don't talk about this outside of work. You work for a marketing company. And so, yeah, I mean, I think that was definitely a big part of the challenge was that there wasn't, there weren't two, there were two other interns with me so I could talk to them about it, but yeah, that I couldn't really talk about it with my friends or anything.

[08:34] Guest 2: Yeah. And this was pretty early. I mean, I think a lot of people are aware of these things now with Twitter and social media, but, uh, this was, this was even before Twitter was out there, right?

[08:44] Ben Dubow: So, yeah, so I'm not that old. It was 2009. Yeah, so Twitter, I guess, was only 2 or 3 years old. Discussion forums were the really big, like, online, online community at that point. Yeah. So it was, it had not really migrated to social media to the same degree.

It was really these kind of obscure discussion boards where you would need, you couldn't happen upon it. You needed to know what you were looking for to find it.

[09:14] Guest 2: Yeah, so you, you kind of went over this quickly, but then you said you ended up doing some work with the CIA. I'd love to hear more about kind of how that happened. And yeah, I mean, you probably can't talk about specifics, but I'd love to hear how something like that emerges.

[09:30] Ben Dubow: Yes, I didn't, I didn't work with them. I got an offer from them. So, and so that process is pretty straightforward, applied through their website. I shouldn't say it was straightforward because it's a government application process and it was just mired in bureaucracy for months and months. Uh, but yeah, so you apply online, get a message back a little while later asking you to take a test. So the test I took was, uh, translation in 4 different languages and then English comprehension test and then, but like being in the tech industry for a while, these timeframes just blow my mind that then it was 5 months later that I went in for an interview.

Yeah.

[10:22] Guest 2: That's pretty fast for the government. Um, so you didn't end up going down that road. Where did you end up next?

[10:31] Ben Dubow: So I was at the— so the place I was interning, I got a full-time role there. Uh, it was, it was a fairly hostile work environment. Uh, my boss, she was an absolutely incredible woman, but she, she had been a spy for a very long time and, you know, had, had legitimate reason for decades. Yes, yes, let's put it that way. So she was not the easiest person to work with. So it was, yeah, it was not a fun place to be.

Was definitely a huge decrease in happiness from the kind of carefree existence you have as a senior in college. So I was working full-time there, but I was really unhappy. So I was just over the moon when I got this offer from CIA. It was going to more than triple my salary. It was going to be doing what I really wanted to do, really fascinating work with really motivated people. So I was really excited about that.

Throughout that time, I was taking the Foreign Service Officers Exam. And so that's, that's always like a year-long process. And they're very front with that. So that starts with a general open to the public test. You go to a testing center and it's one of like, it's probably the most wide-ranging test I've ever taken because it was crafted during the height of the Cold War when Foreign Service officers were supposed to be the most articulate and convincing champions of American democracy, of capitalism, of our values. So you get to know everything from U.S.

history to the name of secessionist groups in Peru in the '70s, to what the different uses of money are, to the difference between debits and credits and stocks, and just everything from economics to world history to U.S. history to constitutional law. Uh, so it was actually fun getting to learn all that.

[12:48] Guest 2: Yeah, that's quite the diversity of, uh, knowledge. How, so how'd you do on the test?

[12:53] Ben Dubow: So I did really well on the written test. Uh, then on the, in on the timed test, then there's a written exam afterwards where you have to talk about examples where you displayed, I think it's 7 or so major qualities that they look for. And then there's a foreign language test where, uh, they just like kind of give you a week frame when they're going to call you, and then you get a call from somebody who just starts like speaking to you in Arabic.

[13:24] Guest 2: Wow. Uh, so, and then there's, so where, where were you when you received that call?

[13:30] Ben Dubow: I was at work.

[13:33] Guest 2: Um, and that's just like an hour-long call and you have to, uh, kind of prove you can, uh, hold your own.

[13:40] Ben Dubow: Yeah. Yeah. It was, I mean, luckily I was working at a place where it was fairly common for people to just get Arabic calls all the time. Didn't lose anything else. Yeah. Um, so then the culmination of that is an in-person group test at State Department headquarters in DC.

So I went down there, and at that point, it's 10 finalists. And I think they only— excuse me, I think those 10 are out of 200 or 300 different applicants make it to that level. And it starts with this group test where they split you up in two, and with the 4 other members, you have to all agree on a plan to move forward with some some simulation that's similar to the type of decisions that a diplomat would make.

[14:36] Guest 2: Got it.

[14:37] Ben Dubow: Yeah, for us, it was pretty straightforward. It's, you want to send a delegation from the country you're in to the United States, who do you pick to join the delegation? Then there is a part of it where you have to write a memo on the best course of action for something you would have to decide as a diplomat. And then there is the in-person exam. And so, or one-on-one or two-on-one. So it's two diplomats that are interviewing you and they mostly ask questions about what you would do in situations they've actually faced.

[15:13] Guest 2: So where did you end up, uh, after, uh, completing that process?

[15:17] Ben Dubow: All right.

[15:18] Guest 2: So is this where it gets fun?

[15:21] Ben Dubow: Yeah. So then, so then there are, uh, So out of those 10, so then they put all 10 people in the same room and one by one they call you out and tell you if you got it or not. And I read all this stuff online about how to prep and like a third of them said you want to be called right away. A third said you want to be called in the middle and a third said you want to be called at the end.

[15:48] Guest 2: So nobody knows.

[15:50] Ben Dubow: Yeah. And so, so they were calling people out and then it was just me and this one other guy and this guy was in my group test and like, I thought he just completely screwed the pooch during the test. So I was like, okay, I didn't get it. Like, whatever. I'm straight outta college. Norm, like people get a master's degree specifically for this.

So whatever. I'll try again next year. And they called the two of us in together and they made us the official offer to the Foreign Service, and it was actually, it was on the 50th anniversary of JFK's "Ask not what you could do for your country" speech.

[16:29] Guest 2: Wow, that's pretty cool.

[16:30] Ben Dubow: Yeah, so when I got out, I, I had NPR on in the car, and so that was playing like as I left getting my offer from the Foreign Service. So that moment was probably the happiest I had been in the year and a half since I graduated college, or 8 months since I graduated college by a lot.

[16:50] Paul: Right.

[16:50] Guest 2: That's like, that's like the ultimate American moment.

[16:53] Ben Dubow: Yeah. Yeah, it was great. Uh, so, so yeah, so was in this situation where after graduating college, sort of everything fell apart for me. Had a job I hated, all my friends had moved all over. Really was just not happy. And then got, at that moment, had offers to two dream jobs.

And it really seemed like I, it was just this year patch when things weren't great and everything was back on track and I was going to be exactly where I wanted to be.

[17:27] Guest 2: So what happened next?

[17:29] Ben Dubow: So I called my, the woman who was going to be my boss at CIA. And I told her that I got an offer from the State Department. It was still going to be a year, year and a half until I got my actual assignment. I would love to work with them until that point. She said, that's incredible, congratulations, my husband's in the Foreign Service. Uh, yeah, that we'll do whatever we can to support you and we'll make sure this works out.

Uh, so like hearing that too coming from a my current boss, like, just was like, oh my God, I'm gonna have an amazing boss, right? Until I get to do my real dream job. So things, so things were like going up even more. Then the next day, the CIA sent me a letter saying that they were withdrawing my application. They cannot give me a reason why, and I should apply again next year.

[18:27] Guest 2: Oh my God, that must have felt terrible.

[18:30] Ben Dubow: Felt pretty terrible. Yeah.

[18:32] Guest 2: Um, and that was the day after you passed the Foreign Service Officers Exam?

[18:38] Ben Dubow: Uh, so I think I passed it on a Tuesday and got the letter on a Friday.

[18:43] Guest 2: Man, that is brutal.

[18:44] Ben Dubow: Yeah.

[18:46] Guest 2: Uh, so where were you, uh, mentally at that point?

[18:50] Ben Dubow: Uh, so I, so my current job kind of alluded to did not pay very much, so I was in this, uh, crappy, unheated, uh, row house with 5 other friends, with 5 other people, uh, in South Philly. And I, like, like, I just went to the basement, there was a rolled-up rug, and I just spent like 10 minutes punching the rug and like had scars on my knuckles for like 6 months after that.

[19:23] Guest 2: That sucks.

[19:24] Ben Dubow: Yeah, uh, so Yeah, so that wasn't a great moment. After I kind of got over the very emotional response came to, I was like, okay, well, I was just staying in this job I hated until I got my assignment from CIA. So now I don't need to stay in this job I hate anymore.

[19:42] Guest 2: Right.

[19:42] Ben Dubow: And I, I'm still going to be a Foreign Service officer. I really can't be that upset.

[19:47] Paul: Right.

[19:48] Ben Dubow: Uh, so as obviously did not have that reaction right away, but when I calmed down and thought about it reasonably, Thought I was still in pretty good shape. So I gave my 2 weeks notice at the job I hated. I figured if I'm going to be in the Foreign Service, I'm going to be in a different country every 18 months. Spent my entire life in Philadelphia. I want to give back for the last couple months I'm here. So I got a job at a nonprofit where we set welfare-eligible kids up with summer internships.

So That was a great experience. Uh, the pay was even worse, but really loved everybody I was working with, great environment, and felt like I was really contributing to my city for the last couple months that I was gonna be there.

[20:35] Guest 2: That's awesome. So how did you end up delivering pizza?

[20:40] Ben Dubow: So because that's, we were setting kids up with summer internships when summer's over. There's really not any need for us. Got it. So it was a temporary job and about 3 weeks before it was going to end, the Foreign Service sent me a letter saying they were withdrawing my offer and couldn't talk.

[21:02] Guest 2: Oh my God.

[21:03] Ben Dubow: Yeah.

[21:04] Guest 2: Okay. So 2, you land 2 dream jobs, they disappear. Um, you are doing something you enjoy at the nonprofit. but that's ending soon. Uh, so how are you thinking about next steps at that point?

[21:19] Ben Dubow: I mean, for, for the, I, I kind of scrambled for a couple weeks and then when it happened, I mean, it was just despondency, honestly. Like, yeah, like, you know, everything, like nothing was as good as it used to be. The shows that made me laugh didn't make me laugh anymore. Food didn't taste as good. Hanging out with my friends wasn't as much fun. Stopped exercising 'cause like I didn't, like I used to go on super long runs.

I would do like an 8 or 9 mile run multiple times a week, but just like didn't like being left alone with my thoughts for that long. Uh, my friend, uh, had taken over his grandparents' pizzeria and said like, if I need some money, should hit him up. And you know, I, I more than anything, I just needed to be doing something besides—

[22:07] Guest 2: get moving.

[22:08] Ben Dubow: Jobs and wallowing in self-pity. So yeah, so I was a delivery boy for a little while. I felt so spurned by my original career plan that I decided I wasn't going to do that anymore.

[22:25] Guest 2: Right.

[22:26] Ben Dubow: I taught myself some web design in undergrad, so thought I could find my way into tech. Apply. I mean, I was really lost. I was applying to everything and anything. That where people would talk to me. And so where I did wind up was this small legal services company where we teach, where we made software to help lawyers keep track of filing deadlines for patents and trademarks.

[22:54] Guest 2: I am guessing that wasn't that inspiring for you.

[22:59] Ben Dubow: So I was so lost going into this. That I was prepping for both the LSATs and the GMATs because I just—

[23:05] Guest 2: Oh no, not law school.

[23:07] Ben Dubow: Well, so having this job, right, where my job was literally to call lawyers and try to get them excited about the features we had to conform with the new USPTO regulation around prior art in pending applications, I was like, this can't be my life. So I stopped pursuing law school at that point. I actually did go through with the business school thing, applied to, and made it to fairly deep in the process for a couple schools. Um, but yeah, so during my year and a half there, it, it was like one of those companies, basically the founder, he, his cousin was at a law firm and was like, I need this software. Here's exactly what you need to do and we'll give you a contract.

[23:56] Guest 2: Right.

[23:56] Ben Dubow: And they just hadn't grown since then. So we were running off of, so this was 2011 through '13 and our product was still running off of Microsoft Access.

[24:10] Guest 2: Oh boy.

[24:11] Ben Dubow: Yeah.

[24:11] Guest 2: So now you're trying to get into the tech world and you end up, so talk to me about how you ended up at Google.

[24:20] Ben Dubow: All right. So, so throughout this time I kept teaching myself web design, uh, trying to get to the point where I could really do it on my own. Uh, the reason I withdrew my applications for business school was I decided to test the job market a little bit and I found a job that I thought was a really good fit. I was going to be doing sales for a marketing as a service company. That was a startup that was actually growing, that had just received some funding. So I went over there and the environment there was just horrendous.

First off, they put me on a QA role instead of a sales role. And my manager repeatedly would not tell me about meetings, get angry at me for missing the meetings, and then ring me out in front of everybody for not being able to tell that a meeting was going on when I wasn't invited to it.

[25:18] Guest 2: Geez, is this about 5 years out of, uh, undergrad?

[25:22] Ben Dubow: No, it's only 3.

[25:24] Guest 2: Geez. So that's, it feels like 5 years worth of stories.

[25:28] Ben Dubow: Oh yeah.

[25:28] Guest 2: So what, what's your mindset at this point about thinking about the real world? Are you just like, I am, I am done with this, or?

[25:37] Ben Dubow: Yeah, I mean, I, I thought, kind of thought that, you know, getting into Penn and getting those offers from CIA and Foreign Service that they were just flukes and that You know, I wasn't, I got unlucky a couple times, but I wasn't really meant for success and like maybe I could aim for middle management someday, but kind of just have to—

[25:59] Guest 2: Oh geez.

[26:00] Ben Dubow: —along until then. So what— So sorry, I got fired from— was the culmination. Got it. What I was thinking after I got fired from that job.

[26:11] Guest 2: So now, now you get fired from that job. When was the first moment you had like some piece of information that was like, okay, maybe there's a path for me out in the world.

[26:21] Ben Dubow: Yeah, it's still a little while away. Oh wow. So, so take, take me where we're going next. All right. So, so I had that immediate emotional reaction again that I was very upset, really despondent. Uh, then, but, but I thought, you know, I had been through this unemployment thing before.

Like I knew what to do. I was much better at interviewing, much better at presenting myself. So like the last one was 2 or 3 months, but I was confident I was going to, you know, get past this in just a couple weeks. And I actually did have some clients for web design, so I could tell people I was interviewing with that, uh, I was a web designer. Got it.

[27:05] Guest 2: So you were working on this side hustle? Yeah. You're taking action on things, you're learning something, um, you're feeling more confident about it in interviews, right?

[27:15] Ben Dubow: Um, yeah, so I interview a bunch of places. Some I make it to the second round, some the third, really don't get anywhere. And then a little while later, you know, I'm continuously interviewing, like my job's to find a job. So I'm trying to apply to 10 or so jobs a day, right? And spending the time doing that, uh, then it just dragged on and on and on. And so before I realized it, it was— it had been 4 months.

And, you know, I— it just seemed fruitless. I— and by this time, so now it's August 2013, and I am 2 weeks away from having to move back in with my parents again. Yeah.

[28:06] Guest 2: Uh, so didn't want that to happen. No.

[28:09] Ben Dubow: So I get these interviews at these 2 really cool, like new tech startups, really excited about them, make it to the second round, make it to the final round. And, um, and both of them, like the final round, they end with some phrase like, oh, we're really excited about getting to work with you. Something that makes me think. 2. And then both of them say that they decide to go with another applicant. So at this point I'm just like, okay, well, back to mom and dad's basement.

Uh, then yeah, so the Friday, Friday, 2 and a half weeks before I moved back in with my parents, I get a call from an unknown number, which is pretty common because I was throwing my application out to to so many places. Guy on the other line says he found my resume on Monster. Would I be interested in working at Google? And I'm kind of like, yeah, buddy, whatever you set me up with a job at Google. Uh, then he's like, hey, I'm having trouble getting in touch with the scheduler, but we're hoping for Wednesday. Just thinking, because the scheduler doesn't exist, this is a scam.

[29:24] Guest 2: Like, Right. So interesting story. I actually landed a job through Monster.com in about 2008 as well. Oh, get out. So I landed my job at McKinsey and Company through Monster.com, which is like so absurd. So shout out to Monster.com.

I don't know if people are using them anymore, but hey, Monster.com, if you're listening, feel free to sponsor me. Two of us would not be sitting here.

[29:57] Ben Dubow: Was it not for you, Monster? Awesome.

[30:01] Guest 2: So yeah, I mean, that, that does sound pretty sketchy. Uh, but it's, I mean, I know you ended up working at Google, so it must've been real.

[30:10] Ben Dubow: Yeah. So we go, so I go into the interview. I didn't know this at the time, but it was the very first interview the person interviewing me had ever given. I had given probably 50, had taken 50 interviews in the past month. So like I was an expert at it. She didn't really know.

So I was able to really make sure the conversation highlighted what I wanted to highlight. Yeah. And next day Google made me, made me an offer to be a contractor.

[30:42] Guest 2: That, that is pretty incredible. Yeah. Um, it's funny how these kind of things happen when you have that, Like, I mean, the worst case scenario, I mean, it's not worst case, right? Um, you have a family you can move into, but I'm guessing you really didn't want that to happen. And these kind of serendipitous things always seem to happen right before those big deadlines. Right.

Yeah. So I'm sure, I'm sure it took you about 3 minutes to accept.

[31:10] Ben Dubow: Well, so I accepted right away, but because I had my offer pulled twice, Yeah.

[31:17] Guest 2: You're like, they're definitely gonna pull this before I start. Yeah.

[31:22] Ben Dubow: But I, I came in like a week from that Monday and it was real. And yeah, the, the first like 3 months there, I, I mean, it was like, it was paradise. It was a honeymoon. So like the last place I had worked, the legal services company, which was Besides the nonprofit, probably the best place that I had worked up to that point, as sad as that was, right? The last place though, there was a year-long argument between the head of the company and the head of sales about whether they were going to replace their 20-year-old coffee maker, and they decided not to. So going from that to unemployment, to then a place where there are literally baristas on staff Right.

Like I just couldn't believe it. And it was just, I mean, that was still like some of the happiest months of my life was when I started at Google. Like things were finally back to where I wanted them to be. Yeah.

[32:23] Guest 2: So you're probably working with people that are like debating, should I do pour over or French press? And you're like, they couldn't even decide to upgrade the coffee at my last company. Yeah. So, uh, yeah. So talk to me, I mean. I think people can go out there and learn about what it's like to work at Google, but I'd love to hear you coming into Google.

A lot of people's paths are— an understatement would be to say not as tumultuous as yours, but coming into Google, how was that for you in terms of the perspective and the scars you had picked up in terms of really appreciating that environment?

[33:03] Ben Dubow: Yeah, I mean, so that was something that kind of bothered me a little was like people were not appreciative as I thought they should be of what they had. I mean, there was also, so the big thing when I first started, and I'm sure people talk about this a lot, is the imposter syndrome. So yes, at my first job, sort of what, what set me apart was like I went to a really good school and I spoke all these languages, and I had a published thesis. And then I started Google. And the woman sitting next to me went to the same school that I did, but a more competitive program there. Her thesis had also been published and had 100 citations where mine only had like 5.

And she spoke better Farsi than I did.

[33:55] Guest 2: Working in those environments, I've definitely worked in environments that with some highly competitive peers and I mean, I was just happy to feel like I was in the middle. Yeah. Right.

[34:05] Ben Dubow: Yeah. So yeah. So at the start, like that's kind of what I aimed for. It was like, don't be the worst person on the team. Got it.

[34:15] Guest 2: So let's dive back in. I know while you were at Google, you started exploring, uh, your passion and kind of interests in, um, intelligence kind of started bubbling up. So how did that emerge again? As a side project at Google.

[34:31] Ben Dubow: Yeah. Uh, so there's like another scar at Google. I don't know if you've already focused too much on that, but.

[34:38] Guest 2: Hey, let's give the people what they want. I think, uh, we can handle one more scar.

[34:44] Ben Dubow: All right. Uh, so, so I, so my role was as a contractor. I didn't get a full-time role at Google. And, but I was basically in a team. I was treated like a full-time employee in every way besides the fact that if you're a contractor, you get a red badge, whereas everybody else at Google gets a blue badge. And you can't— there are like certain places you can't get into, and there's certain events you're not invited to.

There are all these different databases you don't have access to if you're a contractor. Uh, so yeah, so, oh yeah, and so like, so like my orientation, so, you know, like There's probably somewhat well-known Google's orientation where they give the hats and like you do scavenger hunts and all these team building exercises. The contractor orientation, they send you to a room and to like a phone room like this, and you just spent 30 minutes watching this list of things that you can't do, which, which includes riding the scooters.

[35:54] Guest 2: Oh no! That's brutal. No, I think this is a big issue for companies because there's been so much growth in contractors and freelancers and other types of workers, and companies really have to figure out how to engage these people on a deeper level if they want them to do meaningful work. But yeah, so we can table that. Did you eventually get to ride the, uh, the scooters and where did you end up next?

[36:25] Ben Dubow: Yeah. So, so, uh, my role, I was doing optimizations for one of our advertising platforms. And so I was like completely integrated into a team of full-timers. And actually when somebody on the team left, I took over his role, uh, in, in addition to mine, got nothing but positive feedback from my boss. And then when we finally got backfill for his role, my boss decided to give that role that I was currently doing to somebody else that your management knew better. Uh, so I went through, made it to the final round for 4 interviews, which is 20 separate individual interviews.

Uh, and like it was all closely related to what I was doing. So until I got to that last one, I was working every day with people who had rejected me for a full-time job. And I still needed to be super polite, super nice to them, 'cause they still controlled my fate. Right. You couldn't make this up. Yeah.

So then like I had another interview, another set of interviews I thought went really well, but I thought all of them did. Then HR was like, hey, they loved you for this position, but the position no longer exists. And I was just like, of course. Then a week later they were like, hey, the position actually does exist. They made me the offer and I finally got my full-time role at Google. Fantastic.

[38:02] Guest 2: You did it. This is like your, this is like the first sign from the universe that they're not gonna continue screwing you over. Exactly.

[38:12] Ben Dubow: Yeah. So, uh, yeah, so to go back to your original question, like, how did I bring the scars with me? Like, at that point, I was like, I'm never letting myself get in this position again. I'm never going to be on a team that can function without me. Like, my goal, I'm going to be the team, whatever I am on. I'm gonna make it so that like if my manager or senior management thinks about getting rid of me, like they'll lose jobs for it.

Got it.

[38:42] Guest 2: So what are the, what are some of the things you ended up, uh, changing or kind of implementing into your mindset then?

[38:49] Ben Dubow: Uh, so I mean, I not doubled, but I greatly increased the number of hours that I was working. I decided to get really strategic. I like demanded regular meetings with my senior manager. So that we could be exactly on the same page with what his vision was and like make sure that I was implementing it. Everything I did, it wasn't like I, I stopped thinking about how to do my job and like how to accomplish, how do I accomplish the team's goal and how do I make everybody else better on the team instead of just me.

[39:25] Guest 2: Awesome. So change your mindset. You start. I imagine crushing it in this new kind of role. And is this kind of where you started dabbling in that side project? Yeah.

[39:39] Ben Dubow: So just by chance, I met somebody who worked for Google Ideas, which I had never heard of before. And Google Ideas was Google— is Google's internal think tank. They're now called Jigsaw. But back then they were Google Ideas and he was telling me about what he was doing. I told him about my background in intelligence. And he said that they were doing this project to try to get jihadi videos off of YouTube.

And I told him like my job was finding jihadi videos on YouTube, right? Yeah. So the very first attempt all the way back in 2014, and this actually did succeed in getting rid of a lot of the really egregious propaganda. That's awesome. I worked on that project and came up with all of the terms that they based their searches on.

[40:30] Guest 2: So at this point, did you start thinking, okay, maybe this is a path I could potentially explore down the road again? Yeah. Even though it had— you had kind of given up that dream a few years ago.

[40:41] Ben Dubow: Yeah. Yeah. Yeah. Yeah. So that, that definitely rekindled my interest, but my overarching focus was ad tech. I got to the position eventually where I was having a real impact on the direction that our product was going in.

Uh, one of the biggest problems me, my teammates, my extended team all dealt with, basically everybody on this platform dealt with, was our platform just rejected ads at random. So you would have a client upload 100 ads to the system for a campaign that needed to launch the next day, and 16 of them would randomly be rejected.

[41:22] Guest 2: That's not good.

[41:23] Ben Dubow: No, it's not good. Uh, so everybody else kind of just accepted this in my role, at least there was a mindset, you know, it's for product management to deal with. Uh, it's just a crappy platform. Like that's what it is. Right. Nobody wants to end up in ads.

So just like do your job and get out when the opportunity comes. Uh, but I started getting into like really big public fights with product management and started like really upping my SQL skills so I could find the data to disprove everything that they were claiming. Got it. And of that, and like I got really good at politicking too. Like one of the big lessons from the contractor fiasco was get a lot of powerful people to be your sponsors. Right.

So I kind of built this alliance of people from sales and people from support who, who for both of them, like this was the main issue. I figured out exactly what was going on and it took like 100 hours of politicking, but the end result was like these 3 hours of engineering work will increase our revenue by 10%. Like you have. Them. That's pretty fascinating.

[42:42] Guest 2: I mean, in big organizations, it's, uh, I think it can often get so complex, the work you're doing, that you kind of lose touch of what the real goal is of serving the customer, which it sounds like you were fighting for.

[42:55] Ben Dubow: Yes. Yeah. So, yeah, so those got on the roadmap, got a bunch of other feature requests on the roadmap. I was the only client-facing person. On the entire product to get any features onto the roadmap. And those features all solved like the biggest problems that me and all of my friends and everybody that I worked with every day was dealing with.

And that feeling was incredible. Like knowing that my life was easier because of what I had done. Everybody I was working with, their lives are easier because of what they had done. And at that point I was positive I was going to be a product manager on Google's programmatic ad buying platform.

[43:38] Guest 2: Got it. So when did that dream shift?

[43:42] Ben Dubow: So we're now in 2015. Yeah, 2015. Uh, the Paris attacks occur and there's a message I get from one of my clients saying, how do I make sure that none of our ads show up on stories about this attack. And one of my best friends was from Paris, who like sits next to me, and he was like, he legitimately could have lost friends. And, you know, he was despondent, as he should have been. And I was just like, I speak Arabic, like I worked in intelligence, I'm one of the few people who has the skill set to do something about this.

That's got to be my reaction, not how do I protect my advertisers. It's got to be how do I stop this from happening again, right? So, so I decided I needed to figure out how to shift back to that. So I started volunteering with a nonprofit that teaches Afghan women to code. I started doing another side project with Google Ideas, which at that point was Jigsaw. And I started taking Arabic lessons again, started taking Farsi lessons.

I got a new role at Google where I was doing geopolitical analysis for some of our clients, still very sales-focused, but at least, at least like it gave me an excuse to keep up on the news. So with the nonprofit I, so it's funny, for the nonprofit, what wound up helping wasn't that I knew how to code, wasn't that I wrote my thesis on Afghanistan, wasn't that I spoke Farsi. What really helped was my role in tech support at Google. Because I, my role was, it wasn't like crisis is an overstatement because it's ads. Right. But that was my role, was like crisis management.

When the ads aren't working, when the platform's not working and people are freaking out, how do you make sure what happens in the quickest amount of time happens? And so like 3 weeks after I joined that nonprofit, the founder sends out an email about how we're out of money and she doesn't know what to do and we're going to have to close the doors by the end of the month. And I, like, I'm brand new. I don't know anybody, so I don't respond. But then after like 8 hours, nobody's responded. Yep.

And I'm like, well, I know what to do in this situation. My job is dealing with these situations. Right. So I sent out an email like, okay, here is what we are going to do. Uh, CEO, you need to like stack rank our expenses and figure out who were, who's not getting paid, what's not getting paid. Can we like just take a late fee or whatever for these different, for these different expenses?

And when we do that, how long do we have? Everybody else, if you are going to donate, you need to do it right now. You need to send out an email to every single one of your family and friends. You need to post on Facebook, on Twitter, on Instagram about this, and you need to post in your office right away. That Monday I sent out a message to all my coworkers at Google who were unbelievably supportive. With that plan, we got enough to survive for another month.

Then I was like, we also need to— this can't be a surprise to people. We have to have weekly meetings. We have to know how much is in our budget so that we can prep for it. So we started having weekly meetings and started really focusing, getting really disciplined with our fundraising. I had 3 close friends who were directors of development. Oh, including Emily from A&Y.

Yeah. And how, how I can't overstate how helpful they were in making sure that I was doing things the right way.

[47:55] Guest 2: Yeah. Uh, it sounds like this is an extension from that mindset shift of like, I have to be valuable to the teams I'm part of. Yeah. Yeah. Oh yeah, definitely. You're, you're finding.

I'm guessing you're finding like more confidence in like what you're putting into the world, like, um, finding more confidence in yourself and you're starting to pursue the things you're excited and passionate about again. Uh, where does that all end up taking you next?

[48:25] Ben Dubow: Yeah, so, so, uh, I became director of the nonprofit after that episode. Eh, instant promotion. I like it. And as director, I went to this conference in Egypt to talk about what we were going to, what we were going to be, what we are doing. And, and at that point, I was also doing this side project with Jigsaw called Project, called the Redirect Method, where the search terms that I used to look up to get onto jihadi forums, we would serve ads that, uh, you'd serve ads that had counter messaging in them. So what that means, it was YouTube videos from reformed members of ISIS, from moderate preachers, stuff like that.

And it was kind of weird because I was in this position where I was doing this project that I loved, but the most sophisticated metrics we were looking at for how successful it was were just click-through rate out of how— out of all the ads that we showed, what percentage were being clicked on. And then I would— then in the afternoons during my main job, I would go present to Expedia, TripAdvisor, whoever. And if I came with any metrics less sophisticated than lifetime value of a customer over cost of acquiring that customer, I'd be laughed out of the room, right? So That sort of bothered me. I didn't really know what to do about it. I honestly was kind of just happy that it was going on, even if it wasn't as well measured as it should have been.

So I went to this conference in Egypt with my nonprofit, and that's where I met Ivana. And so Ivana had founded her own— she graduated from University of Chicago when she was 19, founded her own startup in Kenya that became the fastest-growing startup in East Africa. Her office was actually targeted in an attack while she was there. She's— yeah. And so she had a somewhat similar reaction to me of how could something this repulsive be attractive to somebody else. So she went way further than I did, though, where I just read a bunch of ethics and morality books.

She actually went to the neighborhoods where the attackers were from. Wow. To get an understanding of what the appeal of these groups were. And that was the start of this massive project she did where she interviewed reform members of the Taliban, of Hezbollah, of Hamas to really understand the appeal of these groups. And I was talking to her and I said I was at Google and she asked me if I knew about the redirect method. And I said, yeah, I set up the search term for it.

And we got to talking and she actually knew my boss from when I was in intelligence. And so we had a connection. She was actually living in Kandahar at the time. So I told her about my nonprofit, recruited her to join the board. And we started working together. And we kept talking about this issue that we saw that there were just no there were no metrics, there was no measurement in this incredibly important field.

And eventually that led to the idea for our company. And I kept do— like I took a week off to do our market research and like I could not believe how antiquated, how unsophisticated this field was. The redirect method, which would not, which like its level of sophistication would be completely unacceptable for an online travel agency. Yeah, was by far the most sophisticated program in this entire field. And I realized with my co-founder, we actually, we were in a position where we could actually change that and could not live with myself if I passed that up. So I could keep a cushy job selling ads.

[52:38] Guest 2: So in some ways you didn't really have any choice but to, uh, go start this. Yep. And it, it sounds like you had this serendipitous, um, uh, meeting with Ivana and it was basically you guys were at the same point and you kind of had to work together. Yeah. So what was, what was the moment you were just like, I'm all in, I'm going, we're gonna do this?

[53:01] Ben Dubow: Uh, so it was like November or December 2016. It was after I did that week of market research. Ivana was coming, so like I had decided after the market research. Yeah. And, uh, yeah, I was just waiting to get to tell Ivana in person when she was in New York.

[53:21] Guest 2: Awesome. So how has the journey been over the last, I guess it's, uh, a little over a year now. How's the journey been of, uh, founding a company and that ride you're on?

[53:33] Ben Dubow: So it's been intense. So I left Google in March and like 3 weeks after that I was, I was driving to some national parks with my friend from San Francisco who had also founded a startup and we were listening to a podcast about Y Combinator and they were talking about how they look for people who don't know what they're getting into because like if they knew how hard it was gonna be, they would never do it. And I was 3 weeks in at that point, so I was like, it's really like, yeah, it's been rough. Maybe we're just lucky or whatever. Oh my God, did I have no idea what I was getting into. Like, I seriously, I, I would make the same decision every single time, but I cannot believe how little information I made that decision on.

I thought it was a lot of information, like I'd really done my thorough research. Yeah.

[54:29] Guest 2: And I've actually talked to a lot of founders who have a similar perspective. They think they know and then they get into the weeds and it's just, it's a million little things you've got to figure out and then so many big things. Is that what kind of drove you to apply to a program like Techstars, which is a similar incubator to Y Combinator? Yeah. Yeah.

[54:51] Ben Dubow: So we, so I gave my very first time giving our pitch. Actually, Wendy Kai set this up. He's also in our volunteer program. Interview. I gave the pitch to Google Ventures. And the pitch was such a goddamn disaster that my co-founder needed to like come in and rescue me.

Yeah. And the guy was super nice. He was just like, hey, I, like, it's still pretty early, uh, but you guys might want to think about an incubator. I'll see if anybody's interested. So he set us up with the Techstars guys. Awesome.

[55:34] Guest 2: So I'd love to kind of change gears here and just reflect on this path of yours. I think A lot of people when they're starting out in their career, right, they think in almost straight lines. Yeah. What, what kind of advice would you even give to someone, um, given what you've gone through? Like you, you couldn't actually give advice to help anyone follow the path you've had.

[56:00] Ben Dubow: No, and I would not advise that anybody follows the path that I'm on. Uh, so I mean, this is much, much easier said than done. But really looking at challenges as an opportunity for growth. And like, I heard that cliché a lot. I really didn't know what it meant. When I was at Google, it was very clear though, the people who had come straight from college to Google or who had spent a couple years at Deloitte before Google or Goldman or anywhere else, you know, really had that path paved.

They kind of accepted things the way they, they were. They would back down when they got pushed back against. And, you know, I would've been the same way if I just had, if doing that had gotten me to Google, just like sort of following directions, then I would not be pushing back and trying to change things. Yeah.

[56:58] Guest 2: And how are you kind of incorporating those lessons going forward, uh, to thinking about how you're just navigating this startup and, uh, opportunities in the future.

[57:09] Ben Dubow: Yeah. I mean, I, I don't think it would've been possible without the challenges that I went through earlier. So maybe a better way instead of the cliché to frame it is view every challenge, like every huge blow you come across, it's just practice for when you're going to face a bigger challenge that matters more.

[57:30] Guest 2: I mean, I, I also tell people like when they're going through something tough, like actually take time to feel like shit too.

[57:36] Ben Dubow: Yeah. Oh yeah. Yeah. Yes.

[57:39] Guest 2: You, you can't actually make those reflections in the moment, but, um, it's, uh, they're definitely great learning experiences. What role has volunteering played, um, in your life? If it seems like that's been a constant stream that's either kept you sane or enabled you to also learn, uh, throughout your journey.

[58:00] Ben Dubow: Yeah. I, I mean, so for all the. Bad turns that happened, I was never really in any serious danger. I have a family that would support me through anything. I could stay with them as long as I needed to, and they wouldn't make me feel bad about it. They would do what they could to help.

They had full trust in me. And that's just part of the unbelievable luck that I've had in life. And like, while this story, a lot of it has focused on these bad strokes of luck, overcoming those bad strokes is only possible because of the incredible good luck I've had to be born into the family I was, to be— to get a lot of the friends in, a lot of the friends that I had. And I've always felt this need to sort of give to give back to people who didn't have the lucky breaks that I did, to try to even things up and to use my luck to help people who did not have the same level of luck that I did.

[59:05] Guest 2: Awesome. I love it. I think that's probably a good place to, uh, end. Thank you for sharing your story. Don't try this at home. And, uh, best of luck in your, uh, continued journey.

[59:18] Ben Dubow: Great. Thank you. Thanks for having me.

[59:27] Paul: Thank you for listening to the podcast. This has been an incredibly fun experiment for me, and I'm loving talking to such incredible guests. I've received some awesome feedback, and I appreciate all the suggestions and just the praise. I'm kind of blown away, uh, It's just so amazing to have such positive support. I hate asking for further support, but would love if you could share or recommend the podcast to one friend. If you are inclined to support more, I've actually set up a Patreon page which I am experimenting with and potentially going to release some exclusive content.

And with the goal of building a community of people who are passionate of making sense of the future of work and enabling people to do work that matters to them. To learn more, you can check that out at BoundlessPod.com.

[01:00:21] Guest 2: Again, thanks for the support.

[01:00:23] Paul: And if you have ideas, questions you want me to answer on a future Q&A podcast, or just suggestions, would love to hear them all. Please email me at paul@think-boundless.com.

[01:00:37] Guest 2: Com.