This transcript was exported on Sep 27, 2019 - view latest version here. Arlan: I'm Arlan Hamilton and this is Your First Million. Arlan: I'm a venture capitalist. I started my fund, Backstage Capital, from the ground up while I was on food stamps. I have now invested in more 100 companies led by women, people of color, and LGBT founders. After having raised more than $10 million, people often ask me how I did it. I created this podcast so I could tell you my story and so that together, we could go on a journey and speak with some of the most successful people in the world from all backgrounds and walks of life to learn how they got their first million. And who knows, maybe I'll reach my first million in personal capital while I'm recording this series. There's only one way to find out. Arlan: This episode is brought to you by DigitalOcean. Let's go. Arlan: Hey. Welcome back to the podcast. It's Arlan. Thank you so much for coming back, taking a listen. Whether it's your first time or you've been around since we started just last month, really appreciate you. Couldn't appreciate your feedback more. You've been subscribing, you've been sharing, you've been leaving comments. You've been tweeting me and posting on Instagram and DM-ing me, it's just been amazing. I can't believe we've only been around for like a month or so. I am stoked about this episode. This is a good one, you all. Get the notebook out. So, we're going to be talking to someone who's had his first million, his second million, his fifth million, his 10th, his 20, and so on. This is Jeff Ullrich from Earwolf and Midroll. He's the pioneer in the podcasting world. It's just as simple as that. Arlan: He, in 2010, started Earworlf which is a comedy podcast network that creates [inaudible 00:02:06] properties. Some of your favorite comedians are on Earworlf. After the success of having this content-heavy really progressive platform of podcasts, he said, "Well, what do we do with it? How do we monetize that?" And he created Midroll to not only monetize Earworlf but to monetize other people's podcasts and help them generate millions in collective revenue. And so, those are really two valuable properties. And just a couple of years, they were purchased. Maybe it was 2015, 2016, they were purchased. Publicly stated, it was something like 50 or $60 million this deal and Jeff, as you'll hear in this interview owned the majority of that. This is my favorite part, because no one would invest in him. Arlan: So, in 2010, he's walking around town saying I have this great idea and I know there's something we can do here and no one would give him the time of day. Only a couple of people really backed what he was doing here. A, his wife, Darlene and B, Scott, his co- founder and they went all in. They went for it. And so, a few years later, it turned into this jackpot for his and his family. And we'll talk about a lot of things in this episode. We'll talk about sobriety, we'll talk ... which is deeply personal for me and for him. We'll talk about the early days of starting this company and then, what happens when you, overnight, are a millionaire. When you go from having not much money at all being kind of broke, to having a little bit of money, being much more comfortable but still, not rolling in it, to then, bam, you are a millionaire. And not even one or two or three million but tens of millions of dollars overnight. 7. Jeff Ullrich - It was 13 vision, 23 luck (Completed 07/12/19) Page 1 of 23 Transcript by Rev.com This transcript was exported on Sep 27, 2019 - view latest version here. Arlan: It's a really, really interesting conversation. Jeff is super candid and generous with his time and information and he doesn't have wall up and you'll see that. This turned out to be only the second podcast interview he's ever done after selling the companies, Earwolf and Midroll. The first one was with Gimlet which as some of you know, I was on Gimlet startup season in 2018 so I know those cats, the episode that Jeff was on is amazing. I listened to it before we did our podcast so check that out. If you dig what you hear here, just go right on over to his Gimlet interview and you'll hear different pieces that were not mentioned there and then, we have pieces that were not mentioned on it. So, it's really a great listen, you're going to hear from one of the pioneers of podcasting, giving you a candid account of what it's like to go from being broke to being a multi-millionaire overnight. Arlan: Thanks for being here, first of all. Jeff: Of course. Arlan: Thanks for coming over to my place. Jeff: Thanks for inviting me. Arlan: You've hosted me in your place twice now and now, you're over here and I feel very honored to have you here. I can't remember what month it was that we met. Jeff: It was September is when we had the party for Derei. Arlan: Yeah, Derei had his book launched. Jeff: Yeah. Arlan: And you hosted a really awesome gathering for him to be able to read from it and kind of galvanize people around his messaging. Jeff: Yeah. Arlan: And you had some interesting people in the room. And I remember that night, I had like a surreal moment because you had all kinds of people in the room and a lot of celebrities. I remember going around the corner to go to your room because you said I could place my magazines ... because I carried my magazines everywhere I go, my cover of Fast Company, well wouldn't ... You said I could place them in your room. So I went around the corner, and I saw Tracee Ellis Ross who I have met before, but still, it's Tracee Ellis Ross, Megan Mullally and Jenna Fischer and you just chit-chatting, just having a ... And it was around the corner. Arlan: So, I promise you, for, I don't know how much time, whatever measurable amount time, I truly thought, for a moment, that I had died and that this was like a hallway to heaven or the hallway to the afterlife. I don't know if I believe in heaven, but it was like this is 7. Jeff Ullrich - It was 13 vision, 23 luck (Completed 07/12/19) Page 2 of 23 Transcript by Rev.com This transcript was exported on Sep 27, 2019 - view latest version here. what happens after and then, there's something that's going to happen next. And I was like, "This is the most surreal ..." And so, first of all, why do you know those people? Why were they at your house? Because we'll get into your story, but I want to know, why do you ... I'm assuming it has something to do with your Chicago background. Jeff: You know, I knew a lot of comedians before, and some of it was from Chicago and I had spent some time in my second city, and so, I had met a bunch of folks there who were older than me because I was training there when I was like 20 and 21 years old and that was very young. But no, I think, you know, I met a lot of folks through my partner, Scott Aukerman who was a very integral part of the comedy world and then, just people coming through Earwolf. I met a lot of people that way, but I didn't really start to build friendships with folks until after I sold the business. Jeff: You know, like you're friendly with people but prior to that, everything, it was like I had employees and I had partners and I had associates and I had talents that signed contracts with me, but there was always kind of like a relationship that had to do with the podcasting stuff and the personal stuff felt secondary to that and you know, I was working a lot. And so, really, it has been in the last several years that I have spent time getting to know people that I otherwise hadn't know. Arlan: Right. And do you feel like people have treated you differently since you sold your company? Or anyone has treated you differently? Jeff: Yeah. I mean I think, you know, I listen to a couple of the episodes of this podcast and this came up before. There is something about people want to ... It's easier to be successful if you've already been successful, people want to spend more time with you if they think that you have some sort of a secret sauce. And so, when you have a successful exit, and in our case, it was the first of its kind in the industry, it's easy for people to have this kind of like mythology around it and you. That makes, I would imagine makes you a little bit more attractive to people who want to be successful, or want to understand how you did it or who appreciate what you did or any of those things.