Your First Million with Jeff Ullrich – Transcript

This is a transcript for Your First Million #7 with Jeff Ullrich.

It is also available in PDF format.

The transcript was created by and may contain mistakes.

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.

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 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.

Jeff:                       Also, I wasn’t available before. I was working 18 hour days, seven days a week. So, I wasn’t socializing. I didn’t go to events, I didn’t go to openings, I didn’t go to premiers. I wasn’t a part of [inaudible 00:09:27], I still don’t. I saw people backstage at UCB on Tuesday nights because my partner had a live show that he produced there and we would do two hours every Tuesday at La Poubelle on Franklin.

Arlan:                    I know la Poubelle. I used to have a wonderful shrimp crepe that they discontinued, but we’re not going to talk about that.

Jeff:                       Right. I’m just trying to show. And so, Scott and I would meet there from 5:30 or 6-

Arlan:                    This is your business partner you’re talking about?

Jeff:                       Yes. Sorry. Scott Aukerman. From like 5:30 or 6 to 8 every Tuesday and then, we walk next door to UCB and hang out backstage and he would produce the show.

Arlan:                    Yeah. That’s the Upright Citizens Brigade …

Jeff:                       Yes.

Arlan:                    … for anyone who live not in LA or hip-

Jeff:                       Yeah. Sorry. So Scott and I, that was our time, was those two hours at La Poubelle and then, going and … Excuse me … hanging out for the show. And so, I would talk to people that come through, and again, you develop relationships and you become friendly with folks but I was not sociable. I was very busy and that was my focus.

Arlan:                    Have you developed a really good filter for people who are coming around, sticking around for the wrong reasons?

Jeff:                       I haven’t found it to be, I think probably as extreme as I’ve heard of other people’s experience. For one, this is only the second interview I’ve done since we sold the business.

Arlan:                    Is it?

Jeff:                       Yeah.

Arlan:                    Oh, the first one was Gimlet.

Jeff:                       Yeah.

Arlan:                    And it was a fantastic interview.

Jeff:                       Thank you.

Arlan:                    We have that history with Gimlet as well.

Jeff:                       Yeah.

Arlan:                    Yes.

Jeff:                       So, I haven’t really told the story. I didn’t do press before I sold the business, I was busy running the business. I mean the banker who sold our company would always comment on how our ground game was phenomenal, but our air game was terrible.

Arlan:                    I mean it’s the way though.

Jeff:                       He’s like you did a terrible job of promoting yourself and telling the story. So, it wasn’t like I had people beating down my door. I mean in the first few days, there was a lot of real estate brokers and money managers and people who scour whatever transaction wires there are, and then, are cold calling you or emailing you or LinkedIn-ing you and trying to get you to give your money to them or buy your house or whatever.

Jeff:                       But by and large, I feel like people have pretty much treated me similar to the way they did before.

Arlan:                    That’s very good. Let’s dig in a little bit about what happened. Let’s just break it down, what is Earworlf? How do you describe it?

Jeff:                       It was a comedy podcasting company that created, distributed, monetized podcasts for comedians. Let’s see. So, Scott’s show Comedy Bang! Bang!, How Did This Get Made with Paul Scheer and Jason Mantzoukas and June. Tig Notaro had a show called Professor Blastoff with us. Jeff Garlin had a show. Sklar Brothers.

Arlan:                    This would have been though years ago, I mean-

Jeff:                       2010.

Arlan:                    Yeah, 2010.

Jeff:                       Is when we started, yeah.

Arlan:                    I mean we’re listening to a podcast right now, this is what we’re producing right now and I just think we’re just so, so early. This is the tip of the iceberg of what’s to come in audio, in general, but in podcast especially, it’s exciting. So, nine-10 years ago, you had this idea, this vision. Do you think it was being visionary or do you think it was paying attention or a little bit of both?

Jeff:                       I don’t know how to answer that question. First of all, the ecosystem compared to today was barren.

Arlan:                    Yes.

Jeff:                       It’s crazy to think what’s changed. I mean nine years ago, I think I told you, 200 yards away was our first studio.

Arlan:                    From where we are right now at my home.

Jeff:                       Yeah. And it was a 225 square foot room with a little …

Arlan:                    Oh, that’s a bathroom.

Jeff:                       … anteroom. So, the studio itself was, I think, about 175 square feet and we had an air conditioning unit in the window that you had to turn off whenever there is recording and it would become a hot box within 4 minutes. Even in the winter, it was so hot in there. We had a hip-hop producer against one wall.

Arlan:                    A lot of bass.

Jeff:                       A lot of bass. And we had a pot dispensary in the next wall, so a lot of stink. People would come out and go for smoke breaks inadvertently right outside of our window.

Arlan:                    Oh, my goodness.

Jeff:                       So when you had to turn the air conditioning off, you could hear them talking through the air conditioner on their phone calls during their breaks. Not ideal for an audio company, let’s just put it that way.

Arlan:                    Yes.

Jeff:                       But it was $500 a month in rent which was all we could afford. We started with $30,000 and we couldn’t afford much. I remember Bob Odenkirk was a guest one day and a roach ran across the green table while they were recording. So yes, very humble beginnings and very close to where we are now.

Arlan:                    Talk a little bit about the 30,000 because I don’t want anyone to mistake that 30,000 from being your little nest egg that you had or that was just a little check you wrote yourself. How hard was it to get that 30,000?

Jeff:                       Yeah. I mean well, $22,015 came from my wife’s Roth IRA. And-

Arlan:                    That she had been saving for years.

Jeff:                       Years. And that was all we had in terms of retirement, anything. We didn’t own any real estate. She had a car. We bought a second hand 2005 Toyota Prius. It was a nice car but like-

Arlan:                    You wife is Darlene.

Jeff:                       Darlene, yes. So, we didn’t have much. And it came time to start the business and we decided we needed $30,000 was like, “Okay. I can put in 6,” and we’re going to pun in 24. And then, the day after, his business manager had said, “I think you should have put in 3.” Yeah, this was not like, “Oh, let’s take 2% of everything we have and just buy a lottery ticket.”

Arlan:                    No.

Jeff:                       This was something we really needed to work. We are betting on ourselves and it was a little scary but not as scary as it should have been probably.

Arlan:                    Right. You probably wouldn’t have done it if you were …

Jeff:                       If I-

Arlan:                    If you’re in your right mind, just really thinking about how tough it could be.

Jeff:                       Yeah. I mean, sure, this is a clean share, right? But if I knew then …

Arlan:                    Now.

Jeff:                       … what I know now, like there’s no way. You know, Scott’s show had a million downloads in the first nine months. And I thought that was something I could build the business around and I did but that’s insanity. That is not something you can build a business around.

Arlan:                    I actually heard you say that on the Gemlit podcast that it is funny now that a million seems so big to you but back them, relative, it was a big deal, right?

Jeff:                       Yeah. Absolutely.

Arlan:                    I mean it was, you were kind of picking up on the right signals.

Jeff:                       Yeah.

Arlan:                    It was just now because of some of the work you’ve done and what others have done, that kind of pales in comparison.

Jeff:                       Yeah. I think just getting back to the visionary thing, I’ve been working hard at least in my personal life to debunk the mythology around like the visionary kind of person. I think that there’s a lot of privilege, there’s a lot of timing, there’s a lot of good luck. Yes, you can work hard and you can have vision but I don’t feel like this … I’ve been compared to Steve Jobs in small little ways and I shoo that, I don’t think-

Arlan:                    I’m going to get like a sound effect that’s like mic dropping.

Jeff:                       Yeah.

Arlan:                    Mic’s dropping. Whenever there’s … I’ve been compared to Steve Jobs, but you don’t subscribe to that?

Jeff:                       No. I mean-

Arlan:                    I’m kind of glad you don’t because then, it’d make you kind of a jerk.

Jeff:                       Well, there’s that too, yeah.

Arlan:                    But you could understand how others might have been impacted and affected by something that you came up with or thought about that no one else did.

Jeff:                       It didn’t feel like it been and it feels wrong to kind of revision this history.

Arlan:                    Right.

Jeff:                       You know, like Scott and I always said, early days, like if we had started three months earlier or three months later, we don’t know that we would have survived because three months earlier almost still too early and three months later, there was more competition already. Scott and his credibility within the comedy community and his ability to listen to an audio file of pilot episode and turned that into li three pages of notes that should cost $100,000 like he’s brilliant, will plug for Scott. His new movie is coming out Between Two Ferns. He’s the co-creator of Between Two Ferns.

Arlan:                    Oh, is he? I love that too.

Jeff:                       And you know, so we had things going for us that were not just me and my brain or me and my vision. There was a time and a place where I got a couple of things right. One was that this was a viable long term medium that was going to grow and was going to be important in people’s lives. That the vehicles for distribution were going to continue to improve, that people’s appetite for diverse content was going to continue to improve and that it was something that did not compete in many ways with other forms of content because you can listen to things when you can’t otherwise consume content … I mean you can’t read or you can’t watch.

Jeff:                       And so, there were a couple of like major tenets of the space that I got right. And then, in terms of our business, I was right when I thought, you know, the issue here right now is that there isn’t talent here. It was essentially a hobbyist deal at the time. And so, we worked really hard to bring talent in the space that allowed people to get excited and to go through the effort of downloading and listening to a file at a time when that was really hard to do. And now, it’s kind of the hard work of working through that early stages of where people didn’t know how to find it. There was no value proposition that made sense and we had to fight through that.

Arlan:                    So really excited about our sponsors for this episode. DigitalOcean. I spoke at their employee lunch a few months ago in New York City at their headquarters and I was just blown away by their team, by their diversity in the room, by their community that they built, the curiosity of thought there. It was really, really fun and they are some really cool. So, when we partnered to sponsor and launch this podcast, I was stoked. Let me you a little bit about what they are and who they are and what they’re offering us. So, DigitalOcean is a cloud platform that makes it easy for startups to launch high-performance, modern apps websites with simple predictable pricing, no gotcha pricing and a UX that developers around the world love, you can stop worrying about your cloud hosting and storage bills and have more time to just focus on your business. We all need more time. That’s not all. They want to make it even easier for new businesses to launch apps in the cloud.

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Arlan:                    Right. And so, for consumers of podcasts, you’re bringing the talent and the content and of course, that was the B2B play too because that’s what they were selling to but for the comedians for themselves, you are providing something that was like a one-stop for them …

Jeff:                       Yeah.

Arlan:                    … so they didn’t have to learn how to become their own podcast producer and seller and all sorts of things. I imagine that kind of changed things too. Were you looking at anything as a model?

Jeff:                       No. I mean, well I was looking at what not to do by looking at TV and movies. So, because of my kind of DNA and my mentality, because Scott himself was a performer and a writer who had a podcast and out of necessity because at the time, these were podcasts and people had to be talked into them. All three of those things conspire to us creating deals that were very artist-friendly because that was like what we believed was the right thing to do and good business.

Jeff:                       So, for once in your life if you’re a comedian and you showed up to do something, you actually owned your IP like we own the masters that we paid to record but you could take your show and do whatever you want with it, you could do derivatives on it like it was yours and that was something that was very uncommon in any creative endeavor in 2010. And then, we also had splits that were … I mean know people have TV shows that they created and their splits are .1% to 5% like a very kind of small, whereas people had 50% splits …

Arlan:                    Yeah. On podcasts.

Jeff:                       … on what we were doing. 30 to 50 I’m sure depending on the show and how much we invested in it.

Arlan:                    But still, just magnitude more than-

Jeff:                       But the money was low. So, in terms of … It’s like people weren’t getting rich in the early days but all of a sudden, somebody gets a $10,000 check and they’re like, “I wasn’t really expecting to get $10,000 from my podcasts,” “Like I can go on a really nice vacation with this”. And the money is what started to attract even more talent because we’re like, look, if you come and you do this and you take it seriously, we can actually pay you for your time.

Arlan:                    Yeah. Because creatives want to be recognized for their talent and gift of skills and it’s not always about just having the cash in hand, it’s not about like this transactional thing, it’s almost like this recognition for your value and your work being worth something.

Jeff:                       Yeah. It’s similar to athletes where people are, “Oh, why is that guy complaining that he only got a $100 million contract instead of a $120 million,” it’s like well, first of all, the owners are definitely doing better in all of these stuff than the athletes so there’s value there and we shouldn’t say that the athletes don’t serve any of it. But you know, if that person’s the best player in the league at their position and someone else is getting 120, I understand why you’re fighting to get that or more because that’s a measuring stick. And because the rest of us can’t relate to those sized numbers, it’s easy to call in to a sports talk radio and criticize that player but I don’t think that that’s fair.

Arlan:                    And you can even get deep with it, it costs so much to be that person.

Jeff:                       Absolutely.

Arlan:                    There’s such a tax to be that person. In the case of someone like Serena Williams, if they’re absolutely the reason that someone like me even watches the game to begin with, you’re not talking about putting a number on her skill which is immeasurable already, you’re talking about re-inventing the game and changing the landscape.

Jeff:                       Absolutely. And for a lot of … Just, I don’t know why we’re going to get [inaudible 00:25:16] to it.

Arlan:                    Let’s do it. Let’s do it. Start … first podcast.

Jeff:                       You know, for a lot of folks, they’re not able to be professional athletes for very long so they have a short amount of time that they can earn money but a long amount of time that they have to prepare to be that good. And so, anyways, yeah, I think that it’s important that creatives get paid properly. By the way, I’m sure, if everyone who ever had a deal with us is listening, 10% of them would be listening to this and be like, “I didn’t get a fair … like I should have gotten paid more for my podcast.” Like you’re never going to make everybody happy but if you have a standard set way of treating people that’s fair, that’s thoughtful, like most of the time, people are going to be happy with that.

Arlan:                    Yeah. When do you think, because it is early times for podcasts, when do you think it becomes on par with having gotten a movie deal or a distribution? When do you think …? Do you see a time period on that? Like we just need 10 more years of going all out in the podcast landscape and it’s on par with every-

Jeff:                       Well, see, forget that … It blows my mind to think that this is the early days.

Arlan:                    Right.

Jeff:                       You know, again, I’m nine years [inaudible 00:26:31] from starting my first podcasting company. But no, I think that it’s already … That shift is happening and it’s where people who started podcasts and are successful at it find that they’re making more money than they are on the TV show that they’re doing and that’s happening.

Arlan:                    It’s starting to happen already.

Jeff:                       It’s starting to happen.

Arlan:                    Well, someone like Joe Rogan and people like that but it’s only a few people, that’s the thing.

Jeff:                       Yes. But even a few people, going from zero to one is a hard thing and so now, yeah, we’re in like the … It’s a handful of people but I think when I sold Midroll, I want to say we had 12 millionaire podcasters that we represented at the time.

Arlan:                    Explain Midroll-

Jeff:                       And that was like four years ago.

Arlan:                    Explain Midroll compared to Earwolf.

Jeff:                       Midroll was a monetization business that essentially supported all podcasters. So whereas Earwolf was like more of like a studio model, a full shop for everything related to doing the show, Midroll have like WTF with Marc Maron is a client and the only thing that we did for Marc was sell ads.

Arlan:                    Monetize the content that you had created at Earworlf?

Jeff:                       No. Sorry. So-

Arlan:                    Oh, for 81?

Jeff:                       Yeah.

Arlan:                    Yeah.

Jeff:                       So WTF was not an Earwolf show. Like Neil deGrasse Tyson’s podcast was a client. Bill Simmons, The Ringer, like that stuff. All of these, we had … I don’t even know what they have now, but at the time, it was like 300 clients. And you know, I had realized that there was a need. I was in a position to solve that problem for people and from a business perspective, it’s really hard to start a 250,000 download every episode podcast. I could sign to a week though to Midroll. It was much easier to grow …

Arlan:                    Yeah, yeah. You were … Well, what’s the word I’m looking for. I’m looking, not agent, what’s that word?

Jeff:                       I don’t even … Because we weren’t agents but we essentially represented all of these shows.

Arlan:                    You’re like a record label, would that be the same kind of …?

Jeff:                       I guess yeah, there’s no perfect analogy. But we helped a lot of diverse podcasts make a lot of money and they sold it, they’re doing a great job.

Arlan:                    And that, correct me if I’m wrong, that is what sold eventually?

Jeff:                       So I created Earwolf with Scott and then, Midroll on my own and then, a company called Howell which is now Stitcher Premium and that’s a subscription business and all three-

Arlan:                    It’s that mic dropped sound effect.

Jeff:                       Yeah. All three of those were packaged in a parent company and sold together.

Arlan:                    Okay.

Jeff:                       So Midroll represented the vast majority, I think it was like 88% of … The value that we received in the sale came from Midroll.

Arlan:                    And was the total sale price ever public?

Jeff:                       Yes. They tweeted it. The Spires tweeted it I think two or three weeks after the sale.

Arlan:                    And what I’ve read was 50 million? Is that what was tweeted?

Jeff:                       It was 50 million in cash and then, 10 million on note.

Arlan:                    Oh, okay. Very good. And so, going back then, while you’re building this over, how many years, when was it sold?

Jeff:                       2015.

Arlan:                    So six or so years of building it? Five or …

Jeff:                       Five.

Arlan:                    Were you balling like were you just throwing lavish parties? I wish people could see the look he gave me. I mean we’re just throwing money in the air and just had our champagne parties.

Jeff:                       No. I mean I didn’t take a salary until the last year. I did take at some … During the entire time I own the company, I took $86,000 in sales commissions because I had previously been selling … doing sales for the podcasters for free and then, at some point, I started charging 10% and I did that for 860,000 of revenue and then, I stopped. And then, I had two years where I got $2,000 a month stipend. So, I got the 86 on the commissions and the 24 on the stipend and then, a salary of 150,000 in the final year. So it’s not like I didn’t make any money, that’s, whatever, 250,000 over five years so 50,000 a year on average I took out of the business but by and large, all the money went back to the company. I didn’t have a car for the first three years and then, I bought a Hyundai Elantra 2012 I think towards the tail end. There were no parties. Well, we had a Christmas at my house.

Arlan:                    Oh, that’s terrible.

Jeff:                       Yeah. It was not nice. It wasn’t the house you were at.

Arlan:                    Oh yeah, I imagine.

Jeff:                       It was a whole another place.

Arlan:                    So what do you think … [inaudible 00:31:33] that, your wife was working still?

Jeff:                       Yes.

Arlan:                    And I mean the reason I really love talking to you is because you’re so self-aware and I hate when people say that they’re self-aware because then, they’re not but I can say it about you, right. You understand your privilege because it’s almost like packaging, right? It has nothing to do with you. It’s the packaging you’re in and it’s almost just logical fact that you have some privilege over other people just like anyone. Right?

Jeff:                       Yeah.

Arlan:                    What do you think … I remember talking to Sophia Bendz who was one of the first employees at Spotify and she lives in Sweden and in one of our episodes, she said, “You kind of start off on the right foot in Sweden because they don’t let you kind of fall.” And that was what afforded her, the ability to fail and try and experiment and not be scared. When you think back on it, do you see yourself as like oh, I had some privilege and that helped me or do you feel like you were flying through pants?

Jeff:                       Well, it can both be true.

Arlan:                    Absolutely.

Jeff:                       You know, I was definitely flying by the seat of my pants although I had a plan and … The thing that was weird was the vision or the plan, the business plan that I had set out with Scott on day one, it actually happened. That, never happens. That it actually works the way you think it’s going to work.

Arlan:                    Like projections and forecasting?

Jeff:                       It was like I was like, “Here Scott, this is what the industry is going to do and this is our role that’s going to be in the industry.”

Arlan:                    And you’re telling me you don’t like the word visionary but you just described what a visionary … I will say it.

Jeff:                       I guess it’s just, I am not special in the sense that lots of people have lots of great ideas and lots of people work really hard. I just, this morning, write a tweet where essentially it was like you know, show me the hardest working person in the world, I’ll show someone who is likely to be living in poverty.” Like let’s get over this idea that it’s working hard-

Arlan:                    There’s a specialness.

Jeff:                       Yeah. The secret sauce, you know, I want to own some part of it. I did see an opportunity. I had the nerves/[inaudible 00:33:47]/ignorance to drop everything and pursue it at potential great personal peril. I worked really hard and I saw through and I executed on my vision. So, like I’m sure, like give me some credit for doing that. It’s not easy to do but I think that’s maybe a third of the story. I think the other two-thirds are all the things. I mean I literally have a list that I made one day, I gave myself 10 minutes to write every single kind of non-traditional or unassuming source of privilege that I had had. And I just kind of brainstormed it out and it’s like, I didn’t have violence in my life. That’s something that I think a lot of people who haven’t had violence in their life don’t think about privilege.

Arlan:                    Preach.

Jeff:                       I had a baseball card collection when I was a little kid and so, I learned math faster than I would have otherwise because I had to figure out certain percentages before they taught you in school. And if you don’t have parents and grandparents who can afford to spend a thousand dollars in 1983, which we didn’t have a lot of money but that’s a lot of money.

Arlan:                    Yeah. Over time, you’re collecting and …

Jeff:                       Yeah.

Arlan:                    Yeah.

Jeff:                       Then, maybe I don’t learn math so quick. The baseball card thing is a big deal. I learned how to buy and sell, I created markets. I ended up getting suspended for running like an illegal gambling operation out of the recess at my sixth grade class. But there’s so many things in my life that I feel really fortunate. I’m an alcoholic. I was an alcoholic for 19 … of the 60 months, the first 19 of the 60 months that I operated the business that is …

Arlan:                    A year and a half of five years, you were what you call a functioning alcoholic …

Jeff:                       Yes.

Arlan:                    … which I relate to in every way. Because you know, built empires while being completely blasted.

Jeff:                       Right. And your kind of an exception too, like it’s not common. You know, it’s the epitome of filling up when you’re able to drink your way through a third of an enterprise that started with $30,000 and five years later, sold for 50 million. There’s something at play there that goes beyond some Steve Jobs bullshit methodology of this like podcasting visionary. I got lucky. I employed people who I was able to pay very little when I didn’t have anything to pay and I probably couldn’t do that today. I basically made up for it by giving people like an acquisition bonus I didn’t owe them because I recognized that if I knew how much I was … That the company’s going to be worth at the time they were earning that money, that I would have given them more but I didn’t have more to give them.

Jeff:                       Today, I don’t think I could have survived with the minimum wage laws that currently exists. Or the way they changed how you look at contractors versus employees. So, that alone, like timing-wise, if I had started the company five years later, the state of California probably would have rightfully prevented me from operating in the way that allowed me to essentially make good later. I wouldn’t have had the resources to do it the right way.

Arlan:                    Was there someone influencing your life or where did you start having so much self-reflection?

Jeff:                       I’ve always been that way but when … Now, I don’t have to work. I have a lot going on in my life but I don’t have a job and so, when you have privilege that turns into success that allows you time, I don’t know. I think it just makes it a lot easier for you to be able to reflect on this. Some of it is running myself with people who are not like me, who have different stories to tell that I can see myself in them in some … It’s like searching for the similarities instead of the differences and I started to realize like overtime, I’m not as special as people told me or that I even thought at one point. And why is that. And it’s my job to unpack that, it’s my job to try and figure it out and then, it’s my job to try and help use what I have to make it better for people who weren’t in the same situation I am in.

Arlan:                    So you’re looking for strength in that? It’s not like you’re just trying to dismantle this as sort of self-deprecating. You’re trying to just kind, to me, it feels like you’re just trying to find this balance so that you can spend all of these years doing it right or continue on that path, to get it right.

Jeff:                       I’m sitting here and just being … Like it’s hard. I struggle with this stuff. I just started seeing a therapist and I label some of how I feel as survivor’s guilt because I don’t know how better to label it. Like it’s not traditional survivor’s guilt but you get a similar like well, why am I the one who gets … to just like go on hikes every day and be a rich guy.

Arlan:                    Because you feel like you got lucky, and two-thirds of it was luck?

Jeff:                       Yeah. Like such a huge proportion of it was luck/timing/circumstance, like whatever words you want to use that isn’t directly assigned to me and my abilities and my vision and all of that stuff. And so, like I have to reckon with that. How much of this is mine versus how much of it was given to me/did I take that I shouldn’t have.

Arlan:                    Well, the good thing is, I mean you’re probably already figuring this out and with your therapist but that could have … If you believe in that space and I think I understand what you’re saying, that money could have gone to someone who is a jerk or who use it in really wrong way or you know, and so, it’s almost like different people have this power and you’re one of them and instead of spending any time beating yourself up about it or fretting over it, all of that time should be like okay, I got it. I got it for us. We’re good. Okay. And now, what can I do with it.

Arlan:                    And that seems to be what you’re doing now on this next stage in your life.

Jeff:                       I’ve been trying.

Arlan:                    Trying.

Jeff:                       But some days are better than others.

Arlan:                    Yeah. Do you ever feel guilty or ashamed when someone says you’re a millionaire? Is that weird to you or is that kind of cool?

Jeff:                       It doesn’t happen, I’d say-

Arlan:                    No one says … Oh, I’m saying it, you’re a millionaire. How does it make you feel?

Jeff:                       It’s very uncommon to have conversations about money.

Arlan:                    Yeah. I found out with this podcast that some people have never really talked about it. This is a really cool situation because … I mean you didn’t have … You weren’t a millionaire before you sold your company.

Jeff:                       Right.

Arlan:                    And then, the day it was signed and things were transferred over, you’re able to kind of look very recently and reflect on how that felt. What does the day after like for you?

Jeff:                       Wow, what was the day after like? It’s so no glamorous, Arlan. I was just exhausted. Getting things to the finish line, it was the hardest thing I did. I mean of all of the work I had done, that seventh-month process of selling the company and especially that kind of last yard was so hard and difficult and exhausting. I was getting no sleep that the day after, I was just tired. The day after that, Darlene and I had taken two days on our own to go to Palm Springs to just relax and celebrate, and we had our babysitter stay with [Arden 00:41:42].

Jeff:                       And during the afternoon of the first day we were gone, we got a phone call that there was a terrible accident at the playground and Arden was on her way to the hospital with head cut open.

Arlan:                    Oh, wow. Wow.

Jeff:                       So, it went from like that to like rushing home during rush hour from Palm Springs to LA just to make sure that Arden was okay. So right away, it was a weird time like it didn’t … That’s the thing that, and I don’t get into this. Now, I’m getting into this, with all these strangers listening, I don’t like to complain about how I’m retired and I have this money but the truth is is that it doesn’t solve all of your problems especially when you have a young child because you don’t … You know, this idea of retired that you grow up with is for people who are older and don’t have responsibilities anymore. The whole point is like you can kind of just relax and enjoy.

Jeff:                       And so, if you don’t kids or if you’re older, sure, it’s a whole different ball game but Arden was three years old when we sold. I still had to wipe her nose and wipe her ass and people still cut you off on the road and you still go to the grocery store.

Arlan:                    And you’re still human, you still bleed.

Jeff:                       Like you’re a person and your daughter falls in the playground and you’ve got to deal with that. And so, it changed but it didn’t change as much as you would have expected. There was that moment of like seeing the money hit the bank account where you just like, it was surreal. It didn’t feel real even though I knew it was … And it felt like you are watching someone else’s life. Because for us, and again, this is different from I think a lot of people on your show, we almost had that lottery winner experience where we didn’t have any money and then, we signed the papers and then, we had all the money. There wasn’t this build up. We weren’t accumulating wealth over time. Every penny went right back into the business.

Jeff:                       I mean we grew 200% a year five years in a row without ever borrowing a dollar from anyone. That’s hard to do, and the only way you can do that is to not be taking money as you go.

Arlan:                    Yeah, reinvesting over and over again.

Jeff:                       Yeah.

Arlan:                    Wow. I mean there’s so many things that come to my mind when you talked about the story of your daughter. I have this thing where I like I’m paranoid, I’m a paranoid person. I’ll say it and I’ve said it many times. I feel like, and I think someone’s … I think it was Brene Brown, someone said that like joy was the hardest emotion for humans accept. I always think it can’t get too good because if it ever did, something else would happen. I get a call from my mom, something’s wrong. When that happened that day, the day after, did you feel like …

Jeff:                       I just-

Arlan:                    Did you feel weird like, “Oh no, is this real life?” Or …?

Jeff:                       No. I didn’t feel that. I remember feeling like a why me after Arden got hurt of like I felt sorry for myself that I wasn’t able to just relax for even just like 48 hours and enjoy what had happened. I mean obviously I wasn’t upset with her, it was an accident.

Arlan:                    Sure. Sure, sure.

Jeff:                       But I did, I did have a little bit of a kiddie party for probably a day after rest, I was like, “All I needed was just a little …” like why couldn’t I had better luck. Yeah.

Arlan:                    Yeah. And as your sort of path to self-enlightenment, do you think today, if that were to happen that you’d have the same reaction?

Jeff:                       No. I’m very different now and I have a different perspective. In a lot of ways … I joked with Darlene that at this point I feel like I’m so [inaudible 00:45:45] I have insomnia. Like it’s actually, it’s to the point where … I have a hard time enjoying things now because all I see is the oppression and the injustice and the systemic kind of obstacles.

Arlan:                    You’re seeing the world through eyes of a black woman.

Jeff:                       I would never say that. That’s very presumptuous.

Arlan:                    In a way, that’s what you were describing, that sort of open wound where it’s difficult to just enjoy things as they are, instead of saying oh, you know, you see the kind of person behind the curtain of what’s really happening and you’re, “Ahhh.”

Jeff:                       Yes.

Arlan:                    And then, you’re in your body and you’re like, “Well, I could over look this and get away with it or I could not and how much energy do I have for the day?”

Jeff:                       Well, the thing is that the epitome of privilege is to see something that’s wrong and not do anything about it because it doesn’t affect you like that’s privilege, right?

Arlan:                    Word. Word.

Jeff:                       And so, you know, when I have bad days, and I have bad days where I’m burned out still and I’m tired and I’m depressed and I feel like I’m not making enough of a difference but I don’t know what to do to do that. You know, I feel like, man, I don’t deserve to feel burned out. I don’t have the right to feel like I’m a little depressed today because there are single parents, single parents of color, single parents with kids with disabilities who do not have the luxury to call in that day and say like, “I’m just not feeling it today. Life’s hard. I need a break.”

Jeff:                       And I struggle with the fact that that is my reality and at the same time, you can see like this is complicated stuff-

Arlan:                    It is complicated, you just [inaudible 00:47:29] it off as like white guilt but that would take the way your humanity.

Jeff:                       You have that whole … You got to put your own mask on first thing, that’s true. I’m not good to anybody if I am so burnt out and all that kind of stuff where I can’t help, so yeah, I mean I’m like trying to work through it and figure it out and talk to people and ask for help and do my best.

Arlan:                    Well, some of my favorite people and the people I look up to or look over or whatever or read about, their entire life was about self-reflection, and I try to do that. I mean I try to evolve every day and try to … The worst thing is making the same mistakes over and over again. And so, just in the act of thinking about it and wanting to be better and wanting to see things through the lens of other people, I mean I think that’s just, it’s miles ahead of a lot of people. And unfortunately, you have this … You’re a businessman, but you had a soul of an artist. I guess because you started off with comedy and writing and things like that.

Jeff:                       Yeah.

Arlan:                    Yeah. Because artists kind of can’t, they can’t be okay with themselves all the time. You’re surrounded by them, so you probably know that, but you know, I would try to find, maybe find 10% less of beating yourself up.

Jeff:                       And that’s the common theme …

Arlan:                    That’s the goal, 10%.

Jeff:                       … of people I spend time with, are, yeah, tell me that, and I’m working on it. But it is, yeah, it’s not easy for me.

Arlan:                    It’s not easy. And so, I mean it’s just one more … It’s just one more layer. This is why I wanted to do this series because it’s one more layer of what is it really like to have a million of something.

Jeff:                       Yeah.

Arlan:                    What is that. Because we’re chasing it. I remember when I was 18, I wanted to be a millionaire by the time I was 21 and then, it would change to 30 and then, it changed to 40 like 32. And in the last five years, I was just like, “I don’t necessarily need to chase that number.”

Jeff:                       Sure.

Arlan:                    It’s not that important to me. And then, it’s funny because things started happening where I can now see that I will be. And I’ve raised several million dollars from my company but it’s like, it’s completely … It’s one of those things of what are you chasing. And then, once you’re there, what’s …

Jeff:                       Yeah.

Arlan:                    So how do you keep yourself busy? You keep saying that you’re retired but I know that you’re doing a ton.

Jeff:                       Sure.

Arlan:                    Your schedule is off the chain.

Jeff:                       I literally just a couple of days ago, decided to stop working on … I starting working on something called the Voting Rights Association and I’m eight months in and I have been looking for a co-founder/ED because I wasn’t qualified or available to run it. It was tough. I had Stacey Abrams on my advisory board.

Arlan:                    I love Stacey.

Jeff:                       I had Vanita Gupta, Kristen Clark, Maria Teresa Kumar, a gazillion like amazing policy advisors. I had a couple of great candidates and I ran out, abstained, like I was so burnt out. I had a hard time doing it and it was really difficult because I made a lot of progress and I care so much about it and it’s like a systemic thing that I could impact. And I called Stacey because I didn’t take anyone’s money yet. You know, people had pledged money but I hadn’t taken it and I had been funding it myself. I hadn’t hired any employees yet even though I had been trying to, it just hadn’t happened yet.

Jeff:                       So, Stacey was my only kind of like stakeholder that I had to call and say like this is where my head’s at and I gave her a little speech about where I was at and how it was frustrating for me but I really felt like I had to stop working on it and I said it’s a bummer to feel like this, I really care about it and she said, “Are you done?” And I was like, “Uh-oh. Yeah, I’m done.” She’s like, “Well, I want to give you some feedback.”

Arlan:                    Stacey Abrams is just …

Jeff:                       “And I want to push back on what you said.” I was like, “Oh no, she’s going to tell me I got to keep doing this.” And my anxiety level went through the roof in a moment and she said, “Well, as far as I’m concerned you had four pre-existing commitments to this. One was your daughter, one was your wife, one was your health, one was your sobriety. And right now, you can’t put those four things first because you’re trying to put this first and you need to give yourself permission,” she’s like, “I don’t want you to use that word failure. You tried, you put a lot of yourself and a lot of your money in to this and you can’t keep doing it and it’s not your fault and it’s okay.” And she basically gave me permission to not beat the shit out of myself.

Jeff:                       So, that’s only has just ended and I actually do feel some joy and relief and like now, I can focus on being a full time dad which is something that I’ve never done it. Always had a side hustle.

Arlan:                    Something.

Jeff:                       Even in retirement of some projects that I was trying to do that was non-profit. But it’s hard because I don’t like the world I see around me and again, I feel like I got really lucky and it was an excruciating process to go through to decide that this was enough. But at the end of the day, I’m no longer the person I was when I started Earwolf. I don’t have the resiliency, I’m still burnt and Stacey is right. I mean she knows me as well as a 10-year long therapist. I didn’t have those commitments when I started Earwolf and she’s like, “The person you used to be like [inaudible 00:53:20] out in the hospital, almost died, wasn’t sober, wasn’t healthy, wasn’t there for your family, why do you keep acting like you want to be that person again? That’s not the person you want to be. Like I like the person you are now and that’s who should be.”

Jeff:                       And so, that’s what I’m working on.

Arlan:                    Wow. Well, Stacey Abrams does it again.

Jeff:                       Yeah. She’s amazing, right?

Arlan:                    She’s the real one. Yes.

Jeff:                       Yeah.

Arlan:                    And it seems to me that you … You haven’t spoken about this but I’ve seen it, you catalyzed other people and that in itself, I mean can be even, that’s a scale of a way of getting some of the change that you want to see made and have it happen without having to put yourself, rake yourself through the coals.

Jeff:                       Yeah.

Arlan:                    So that’s something that you feel like … You feel comfortable with that pocket?

Jeff:                       Yeah. I mean, because I don’t know, for whatever reason, that is something that feels very doable for me is things where I just have to show up and do a thing and it’s useful to someone. And even if I do that over and over again, since they’re one time things, none of them feel like a commitment that’s too overwhelming to sign up for right now. I don’t know what the future brings, I don’t know … And I’m 44, I don’t know if I never feel capable of starting anything again or if that changes or if I do just stay in this lane where I’m opportunistic and I look for things that I feel like I specifically can add a lot of value to that I believe in and then, I just write the check or show up to the thing or make the calls, you know what I mean?

Arlan:                    Yeah.

Jeff:                       Whatever it is I can do. Yeah, I’m in a bit of identity crisis right now. I don’t know who I am or what I’m going to be so I have to figure that out and I have to give myself a little bit of permission to have space to do it.

Arlan:                    Absolutely. And you are young and you have kind of the world at your fingertips now because of the fortune that’s come in. And I guess it’s going to be about how you wheel that, if you let wheeled you or the other way around.

Jeff:                       Right.

Arlan:                    But yeah, please take as much time as you need to figure out what you want to do or not figure it out.

Jeff:                       Yeah.

Arlan:                    I mean you know, like the … I think everybody around you and Stacey’s showing that, it’s like everybody wants you to be okay, like just to be okay with yourself and you’re healthy. It’s almost like don’t be afraid to come out of the closet because all we want is a healthy kid, you know?

Jeff:                       Yeah, yeah. Right.

Arlan:                    It’s just you … The expectations from your friends and family are that they can be around you.

Jeff:                       Yeah. Right.

Arlan:                    That’s the thing. Well, thank you so much for this. I think it’s … I’m going to probably have to have an entire season of this series that is just part two of every conversation I have because you’re just getting started and I’d love to learn so much more about your journey. But I really appreciate you being here.

Jeff:                       Thanks for having me.

Arlan:                    Yeah. And I will … Any time Tracy’s over at your house …

Jeff:                       Okay.

Arlan:                    You call me. If you need me to deliver some pizza.

Jeff:                       Right. Yeah.

Arlan:                    Or help you with the … whatever you need, I’ll be there. All right, Jeff, thank you so much.

Jeff:                       Thanks, Arlan.

Arlan:                    Hey, so I’d love to talk to you and keep the conversation going. Find me on Twitter and Instagram at Arlanwashere, that’s A-R-L-A-N was here. Stick around too because I will let you know when my new book is going to be in pre-order. Now, that’s coming out in 2020, it will be out. It’s a real book, oh my goodness. And you will be able to pre-order it most likely this year so stay tuned, I’ll let you know all about that on Twitter, on Instagram and on this podcast.

Arlan:                    Thank you again to DigitalOcean for sponsoring this episode. If you are interested in sponsoring an episode of Your First Million, get in touch with me. Right now, it’s easy to do so. You just email me at arlanhamilton@gmail, that’s A-R-L-A-N And put in a subject that you are thinking about sponsoring and I’ll give you some more information. This is a really highly-engaged audience, really, really educated either through traditional means or through grit, tenacity or a little bit of both and yeah, these are the people you want to be talking to. You’ve got aspiring founders, you’ve got in the trenches founders, you’ve got aspiring angel investors and active angel investors. You’ve also got venture capitalists, you’ve also got limited partners. And then, you have people who are listening in to learn all about what all that means. And so, it’s a really interesting group of people. Check it out. Thank you again, DigitalOcean for sponsoring.

Arlan:                    Your First Million is produced and edited by Anna Eichenauer and Senior Producer Bryan Landers. Additional audio mixing and mastering by Alfred Hamilton. Additional production by Chacho Valadez. Executive producer, Arlan Hamilton.