Breaking up with my girlfriend changed my life *crazy* | vlog #49

We broke up and I was like, I was actually in a really shitty place. I was like, fuck, like this sucks. I like love this girl. So it's not like I can just not think about it. I'm like, I go to her house to sleep. Ryan gets back from Israel like, like soon. Trying to catch it. What's up, man? How you doing, bro? How's Israel? Sick. I actually need footage. Ho boy, stop stuntin'! Alright guys, so just got my sick new iMac set up and I'm about to come back to the office in like 15 minutes. We'll see you guys in a little bit. Whoa, whoa, whoa! What just happened? That was the craziest thing ever. First we time travel, now we just get haircuts? We're ready to go on a serious note though. We have a lot to do this week. Um, one of the things that I'm actually doing today is I'm cleaning up all of our sales CRM so that we can track all of our demo metrics a lot cleaner. Right now, the data isn't really clean where we can just extract it and like pull it, pull reports very easily. So I'm creating custom fields and everything so that we can easily track the stages of our sales funnel and like hold the reps accountable more. And then also I'm creating different stages as well so that we can see like how leads are passing through each stage. And, uh, I'm playing tennis at 6. Going to play tennis with my boy Matt. We had a little quick session at the office today. Now me and my friend Matt DeVoe, we're playing tennis here on the East Side. It's actually gorgeous. That's the Brooklyn Bridge up there. And I am going to time-lapse this whole thing, this whole little sesh. We're about to roll a clip right now that I recorded a few days ago with Haley. We were in her apartment in Tel Aviv, and we basically tell the entire story about about how we started dating about 8 years ago and then we broke up about 5 years ago. The whole story and the whole idea behind what happened and why it's funny and relevant to all of this stuff is because I used to— I was living in New York, moved to Virginia because I was dating this girl, and then we ended up breaking up. It sucked. I was living in rural Virginia. I was literally like working at this huge like corporation and I didn't really like it. But what happened after we broke up was crazy, like life-changing stuff, and it like changed like my life and my family's life. Roll the clip. I'm gonna tell the entire story. Haley and I were dating. I'm just gonna tell the whole story, but basically how I used to work started this startup. I moved to Virginia, how the mHelpDesk thing happened. We got acquired by IAC, then PhoneWagon started. We're gonna tell the whole story. We were dating in college, uh, my end of my junior year all through my senior year. Then I graduated on time, obviously, in 2010. I moved to New York City and I was working at Yext, which is a startup. Um, back then what I was doing is I was on the phones doing sales, calling into local businesses, and we were selling leads. So that's when I sort of got introduced to one, startups in general, call tracking, and I got in sales, right? Because I After Clemson, I was like, oh, I'm gonna, you know, go to Wall Street, but then I realized that like I wasn't smart enough and also that no one was recruiting random like 3.0 GPA Clemson grads. So then the finance thing didn't work. I got a sales job at a startup in New York City, moved to New York, and I was, I was doing that. So every single day I was literally like cold calling into local businesses selling like advertising, which was leads, paper call leads, and that sort of thing. I was dating this girl literally this girl, and I was like, oh, alright, I'm in New York and I'm cold calling. Like, this is kind of annoying. Like, should I move to Virginia? And I don't even think you pushed me to. I think I was probably like, I wanna move to Virginia. No, you probably told me to. Well, you're enthusiastic about everything. Yeah, yeah, yeah, super into it. So I was like, yeah, so I'll totally leave like this startup in New York and I'll move to very rural Virginia. It wasn't like Arlington, Alexandria, any of those cities, Fairfax, Reston. It was like Leesburg, Herschelburg. We literally drove across the road. Yeah, cornfield. It's like a corn maze. Yeah, yeah, yeah. So then I moved to Virginia and I'm literally working at her dad's company. I was doing my own thing, you know, I was working in sales at this startup in New York. Somehow I was basically like living at their house. So it was basically me in Virginia, rural Virginia, living like literally at your house, working at your dad's company. And by the way, there's like pictures of them on the wall, so it's not like I'm like stealth. It's like I walk into work every single day, there's like a photo of them. So it's not like I like am not reminded of it. And I think I'm just like, you know, doing my own thing. It's like literally like photos on the walls. I'm like, oh my God. I have a bust of my dad in his cubicle. And by the way, I was also like the kid that's like dating the founder's daughter or whatever. So it's like, I think people were just like wrote me off as the joke awkward. And then here's the thing, here's the thing that's crazy. And then we broke up. Really? She's like, oh, I'm gonna start— Broken heart. I'm gonna start riding horses and like traveling, I'm like, yo, I gotta like work in my cube. And then like, I figured you'd wait for me until I was back. You're still— you're in Israel right now. You're still gone. I'm still waiting. You're still gone. I'm like traveling to like the Middle East. Like we broke up and I was like, I was actually in a really shitty place. I was like, fuck, like this sucks. I like love this girl. I love you too. I'm in Virginia right now. I'm like literally working at her dad's. So it's not like I can just not think about it. I'm like, I go to her house to sleep. I walk into work and there's pictures of her father, you know, so it's like it's everywhere. It's not like I can just like out of sight out of mind. It was like in sight in mind. I couldn't get away from it. But this is where it's crazy, and this is where I'm like, hey, when things like that happen, you know, you just have— one, I feel like time fixes everything, by the way. But also it's like you have to just know in your head that like good things are on the other side of it. Because what happened at this time, literally as we were like breaking up, I met up with Vincent at this event in Washington, D.C., which one, I wouldn't have gone to the event if I hadn't been working there because I was working at her dad's company. Company, and they were like, oh, you got to go to the event because we sponsored the event. So I like went because I was like the young guy that they were like just made go to the event they sponsored. So I went to this event in Washington, D.C., met up with Vincent, who was already doing mHelpDesk along with a couple other startups and stuff. So I went to the event, met Vincent, and was literally like— so then we were already in conversations like, hey, how can we work together? And I was like, look, this company's massive, it's gonna be difficult to do things. As soon as we broke up, I would already been talking to Vincent, so I was like, look, it's time for me to I have to like pull the trigger and go full-time on this thing, right? Like, I can't just be sitting here at my ex-girlfriend now's dad's company. Like, that's just weird. Like, I need to be like my own person, you know? So it helped me really like pull the trigger and jump ship and be able to go full-time on something. And the crazy thing is that I had so much time, by the way, that I was able to go all in. It's like I didn't have like a girlfriend anymore, and I was just like in this area. There's not— there's just like cornfields everywhere. So there's like— you're Yeah, I ended up joining Vincent. We went full-time. We literally went all in on mHelpDesk and thing like ended up working, right? We ended up figuring it out, how to sell it. The product was there, the timing was right, the market was super hot. This was like in end of 2012, 2013, 2014. Literally in 2013, we got 3 acquisition offers. It was like life-changing amount of money and we actually turned all 3 of them down and then we went heads down. We ended up like taking the company all the way to $1 million in annual recurring revenue before we even raised any outside money. And then in the end of 2014, we got acquired by HomeAdvisor, which was like insane. And I was literally 26 years old. It was a life-changing amount of money for me. I didn't come from any money at all whatsoever. It was like crazy because it wouldn't have happened, one, if I didn't move to Virginia. It wouldn't have happened if I wasn't working at your dad's company and I was forced to go to this event, and then that made me meet Vincent. And then it also wouldn't have happened if you didn't break up with me, because I probably wouldn't have like pulled the trigger. I would have just been like comfortable and like chilling there and like cubicle. It was a fire under my ass. It's like, hey, I need to like do something with my life and I need to like figure it out and like be like prove to like the world, or maybe just to myself actually, that I can like do it. Because I was kind of feeling like sometimes when you get like handouts, you like feel like you're— it's like, it's almost like you don't deserve it and stuff like that. But it's like, you know, personally, if you're like confident enough, like, yeah, I can do this. Which kind of goes back to the point of like, it sucked at the time because I was like devastated and I was like lonely and like all of these like emotions and stuff like that. But like coming out of it and being on the other side, it was like this crazy like— You made me feel bad. Why? No, you shouldn't. But the thing is, it's like this life-changing like event that happened for me that now is like literally putting like myself and my family in like a better place that like it would— we wouldn't have been in like had all of that stuff not happened. Like literally my dad retired like early because of like all that stuff that happened and I'm able to I'm like crying. I know, I can see it. If you guys are like feeling down or if like weird things are happening and it like sucks right now, like believe me, I went through like not even just like days or weeks, like months. I was like, this freaking sucks. Like, fuck this. Like, I don't know what I'm doing. And the thing is also when you do a startup, it's like pretty lonely anyway because there's not like other people and it's like, and even once you start hiring people, you can't really hang out with them like and super like connect because they're like gonna be your employees. So then there's this like awkward dynamic and stuff like that. So I definitely went through like all these like weird times where it like felt low and stuff, but coming out of it on the other side, you know, just proves to you that like don't let little things like get to you and like you think that it's the end of the world because there's gonna be something that is gonna like come from it that can be potentially life-changing. I feel like I should be your example of that. That's the point. Thanks for breaking up with me. You're welcome. And I think this is gonna be like, hopefully you guys can take something