Episode · Mar 4, 2026 · 1 hr 40 min
From Prison Yard to Venture Fund
with Daniel Dart
Daniel Dart is a venture investor who founded Rock Yard Ventures after serving time in prison.
“once I'm your friend, I'm like extremely loyal. I'm extremely reliable. I'm extremely consistent.”
Summary
Daniel Dart describes a volatile childhood, time in placements from age 13, and years of homelessness in Southern California. At 18, he took a plea deal in a kidnapping and carjacking case that carried a 150-year sentence. He spent years in county jail and prison, challenged the conviction on appeal, and accepted a reduced sentence that let him leave prison. After release, he got sober, changed sheets at Airbnbs, and began seeking out people whose work and habits he admired.
Music work led Dart into criminal justice policy, international development, and jobs connected to the World Bank and Bezos Family Foundation. He studied at the London School of Economics, completing two master's degrees, then earned an MBA at MIT. Dart tells Ken that a bank refused to work with his new fund because of his record, while other allies backed him. He built a prison financial literacy program, launched Rock Yard Ventures, and now invests in critical industries. He is also seeking a California governor's pardon.
Show notes
Daniel Dart is the founder of Time Again, but before music, before venture capital, before MIT, he was homeless, gang-affiliated, and sentenced to decades in prison on kidnapping and carjacking-related charges.
After fighting his case on appeal and earning a reduced sentence, Daniel rebuilt from nothing — working housekeeping jobs, getting sober, and deliberately surrounding himself with “winners.” That path led him into international development, work connected to the World Bank and the Bezos Family Foundation, two master’s degrees at the London School of Economics (without traditional prerequisites), and an MBA at MIT.
Today he runs Rock Yard Ventures, invests in critical and foundational industries, and is pursuing a California governor’s pardon.
This is a conversation about prison politics, systemic failure, stigma, merit, second chances, and what it actually takes to rebuild a life from the ground up.
Transcript
Made from YouTube's automatic captions and lightly corrected, so a few words and names may be off. Click a time to play the video from there.
Ken Rideout
Daniel Dart, welcome to the show. Thanks for doing this, brother.
Daniel Dart
Man, thanks for having me. I'm excited to dig in.
Ken Rideout
Fellow uh finance bro.
Daniel Dart
Yeah, dude. I'm a hardcore finance bro. You can tell.
Ken Rideout
You look just like one.
Daniel Dart
It was always my dream actually, you know. So, it's like I'm excited. Like some people always complain about being corporate. It was kind of always my dream to get here.
Ken Rideout
When I tell people about you, I'm like, dude, this guy was like a musician, went to prison. Yeah. Even I I'm sure you're going to tell us about the charge, but on kidnapping and carjacking. Yeah.
Got out. Did you not graduate from high school?
Daniel Dart
Uh, I got like a GED.
Ken Rideout
You have to be the only person in history that has a GED, then went to London School of Economics and MIT.
Daniel Dart
I think so, actually. Yeah. I think I think I was the first person to ever go to London School of Economics without the prerequisites. And then I know I was the first guy who was formerly who went to MIT as well.
Ken Rideout
That's incredible. Well, the thing is with those schools, like it's you can't fake your way through the intellect. that's required to get into those places.
Daniel Dart
Yeah. I think um it's pretty wild sometimes like looking back on it while you're in it, you don't really think about it. Like you know, you're like in the fight, you're not watching it, so you don't realize. Now looking back, I'm kind of like wow, oh my goodness. You know,
Ken Rideout
That's a good point. Like when it comes to running and people like you won this, you won that. I'm like I guess from an from the outside looking in, it looks like whoa, you did a lot of stuff. But I always think, dude, that's my survival story. I was never thinking I'm going to win races. I'm going to do this and do that. I'm like, I need to run today to stay sober. And it just so happened that the more I ran, the faster I got.
It was never like, I'm running so I can win races. That was a byproduct. Yeah. So, it's the same kind of thing except for me, I so many of my formative years when I was younger was homeless. And not like homeless like on a couch. Yeah.
Daniel Dart
But like homeless homeless like living on the street, begging for food, you know? I think as life got on, I have this fear that I'll be homeless again. And so everything is like what can I do to avoid that and and you know you end up overcorrecting I think in many cases but a lot of times when people see homeless people I don't know if they actually look and go wow that could actually be me.
Ken Rideout
Yeah.
Daniel Dart
And so a lot of that is hey I don't want to be there. And then also I think once you really apply yourself which I think most people never do their entire life. I think I'd say 99.9% of people do just enough to get by or just enough not get fired. Once you actually apply yourself and you see what's possible, then you kind of want to do it more because you're like, "Shit, I can do this." Which, yeah, I would expect was is the same for you because you uh recently won everything at the Austin Marathon,
Ken Rideout
At the half marathon. I won the Mast's division over 40 at 55. 55 in two months. But let's start at the beginning because I'm so intrigued by all of this. Like, how the hell tell me about your childhood and how you ended up homeless.
Daniel Dart
childhood was was all over the place. And a lot of times,
If people have seen the the TV show The Bear or Shameless. Yeah.
And to me, it it kind of seems normal. I think there's a lot of families in the US, especially in the 70s and 80s.
And I don't want to use the term dysfunction. I think it was just a different time.
Ken Rideout
Yeah.
Daniel Dart
Right. It wasn't like therapy. It wasn't like, hey, let's sit down and talk about it. It was just kind of like, yo, let's smooth over the broken parts and like figure [ __ ] out. And so there was just a lot of volatility. And as a result of that, I think, you know, and my parents will probably listen to this. They're great people and I love them. I I think sometimes they were really great with man-on-man defense, right? Like two kids. I think at three kids sometime they switched to zone.
Probably not their their focus. And I think the tools that were available then are a lot different than the tools that are available now.
Ken Rideout
Yeah.
Daniel Dart
So I ended up in placements really from age 13 on. And I think when you're young and you don't have a stable unit, you end up looking to your peers for that stability, which you know leads to gangs or drugs and all of these different things.
And then not only does that compound, but you lack the maturity or the wisdom or the network or the resources to get out of it. And so when I was 18 and and been in and out of lockup for I don't know a year or two already ended up getting arrested again for joy writing um and shoplifting and at the time again didn't have any maturity ended up like taking two years you know like it was like oh plead out to this like in retrospect I totally got [ __ ] uh but you didn't know cuz you're a kid and it's crazy what the what the public defenders and what the system will allow you to do to yourself just for the and It's all for aesthetics for them.
Yeah. We got this conviction and you're like, "Dude, that's like a young kid. You could you had the ability to change his life for the positive, but you wanted to get a conviction and you like threw him like under the bus." Yeah. And I've given this a lot of thought. There's there's very few things in my life I have resentment on. Almost nothing. I think that situation I I have resentment for because you know you're really just taking advantage of young kids and traditionally and this and and I'm gonna kind of like sidetrack into just the criminal justice system.
I have high opinions that we shouldn't charge minors as adults ever and people are like well what if it's 17 and they shoot 10 people. Well then you should revamp the whole system. If there's a 17-year-old genius who's at Harvard he can't vote, he can't drink. He can't do any of that. But then we're going to take like the most [ __ ] up 17 year olds and say like you're an adult. And I just fundamentally disagree with that. And I know that it's not as zero sum as I'm painting it out to be, but I'm trying to use that as an analogy that like young kids are young kids.
And so at that time Yeah. It totally [ __ ] my life. I ended up getting out, you know, like a year later and the internet wasn't a thing yet. So like when you lost touch with people, like they were just gone.
Yeah. And so I ended up getting released down by the border near San Diego. And because I had been in placement since I was 13, I didn't really have a friend network to go to. I didn't really have any friends or still really from childhood. I just had nowhere to go. Wasn't in touch with my parents and ended up really on the streets for almost like the next two and a half years.
So wait a minute.
Ken Rideout
You how did you lose touch with your parents when you got out of jail? You couldn't call them or were they just frustrated with you? I I frustrated and it's like it's hard because I think it's really easy to look back and judge now. I think sometimes people like, "Oh, how could your parents do this? How could you do that?"
Daniel Dart
And do I think we would both do things differently now today? For sure. For sure. Like we're both much wiser. I think at the time I think there was a lot of resentment, a lot of problems that they had to work through in their own life. And I think unfortunately, you know, I didn't have the maturity to engage and and they didn't have the maturity to engage. To be quite candid, things were so volatile as a child that it was never even like, hey, let's reach out to them.
Ken Rideout
I got you.
Daniel Dart
Like, it wasn't like, yo, I want to rush back to that. It was more of like, yo, this is [ __ ] being on the streets, but also that like
Ken Rideout
is [ __ ] But that really I hope for the audience paints a picture because I had I wouldn't say that I had similar situation in the sense that like I would probably call them and go back even though it was hectic and chaotic. It like really shaped my life. Like I have a brother who's 11 months younger who was in and out of prison at lifelong heroin addicts.
Never had a job.
Always like either sold drugs, was into like just corruption and in and out of prison under the same roof as me. Once I left there, I never went back. back and I wish I had the maturity that you have to be like, "Oh, everything's great now. Yeah, I really liked it." But I'm like, "No, [ __ ] all that. I don't want to like I just keep my distance." I don't even like to think about it to the point where my wife will be like, "Who was your favorite teacher?" And she thinks I initially I think she thought that I was bullshitting, but I'll be like, "I can't tell you a single teacher's name." Maybe one or two, but like I don't have memories like that.
I my it was so traumatizing. I've blocked out like parts of my life that I genuinely can't I mean I remember like themes but I don't remember like names of teachers. It was just ugly. But I would have thought
Versus being homeless. I'll go back there. Like that to me is intimidating.
Daniel Dart
Yeah. And I mean being homeless was [ __ ] nuts, you know? Like especially being involved in gangs and all sorts of [ __ ] Like there was just so much volatility that came along with that, you know. Now I'm in finance. We we talked about like the thing that I always preferred about being homeless where at least it's my own volatility is like I'll bet on myself a 100 out of 100 times.
Ken Rideout
Yeah.
Daniel Dart
So like when I'm in a hairy situation like I want to be the one that's in control.
Ken Rideout
Yeah.
Daniel Dart
And so I think that it kind of saved me over time whereas like the minute you hop into other volatile situations you put yourself
In other dangerous things. And I think like the one thing about being homeless um is you can some extent manage your environment in a way where you can get isolation.
And I think at that time that was really helpful. And even now a lot of times people think I'm an extrovert but I I really am very very happy alone. I think I prefer to be alone almost all the time.
Ken Rideout
So where do where did you grow up when you were getting in trouble and getting
Daniel Dart
So what I'd say is the first part of my life up to 13 was in Northern California. And then, you know, I say 13 to be honest, Southern California.
Ken Rideout
Yeah.
Daniel Dart
And then homeless primarily in San Diego and LA. And then also like I would end up in random places because like I would just like hitchhike. I must have hitchhiked in my life. I don't know maybe 5,000 times. Like more times than I can count almost every day for a couple years. Like I any place I need to go, I just go to a gas station be like, "Hey, you headed this way?" And someone would take me I'm going this far. Like all right, take me that far.
And you know, then I'd hop out. And I was always kind of adventurous or or fearless. I don't know it's the right word, but maybe courageous where I was like, "Hey, I'm going to figure it out."
Ken Rideout
Seemed like you were adventurous. That's how I would think of it.
Daniel Dart
Yeah. Yeah. I It's weird because looking back, there's a lot of times that I'd never want to relive, but also some of the the best times of my life.
Ken Rideout
Yeah.
Daniel Dart
You know, the same as is prison, you know.
Ken Rideout
We'll get into that.
Daniel Dart
We'll get into that. Yeah.
Ken Rideout
I mean both. It was formal gangs. like what would be the name of a formal like white kids gang.
Daniel Dart
So I was I was involved in all sorts of gangs and I won't get into it but
Um definitely like formal formal gangs but I think the thing about it is growing up how I did
I spent a lot of times with different races. So like
Ken Rideout
Oh I see I see what you're saying that okay that makes sense. And I know that like from being in from working in a prison for four years and then have
A gazillion friends that were in and out of prison and then interviewing a million people from prison. I know that when you go to prison and you're a white guy, like it's not like you don't have a choice of like, "No, no, I'm just I'm I'm out here by myself." It's prison is like, especially California prison, from what I understand, it's like, you know, no, you want to be alive, you hang out with your people, we'll hang out with our people, and it's segregated and there's no gray area.
Even the even the guards, uh, to a certain extent, right? They
Daniel Dart
Yeah, it's it's hard because I think, you know, I think I got unique perspectives on prison from other people. Um, and first I I'll I'll kind of touch on the thing I said about some of the best times. The first time I went upstate, I remember talking to an older guy being like, "Yo, what's what's prison like?" And he had said something along those lines. He's like, "The weird thing about prison is like, it's going to suck, but also like you're going to meet some of your best friends there." And he's like, "You're going to have some of the best times in your life, and it's really hard to understand until you've been through it." And he's like, "I'm telling you that because like you will survive.
You will be okay. Like don't get in your head about it."
Ken Rideout
That's easy for you to say.
Daniel Dart
It's easy for you to say. And like there was some crazy, you know, riots and [ __ ] like that. But I think the thing about prison, and I'd always say this, like every time I touched down on a yard, I'd always say like, "Hey, I'm not a prison guy. I'm just a guy who went to prison. Like I'm just passing through." Yeah.
So I don't want no problems. I'm just going to read my books. I'm going to read my paper and I'm really going to try to avoid as much as possible. And then I got some other really good advice when I first got there that was like the minute you hear anybody say anything negative, just like get up and walk laps, you know, like we'd always say, "Oh, I'm going to go spin laps, which means just like walking in circles around the yard." I think that was the best advice I got there.
And like because you know a lot of times negativity is the unifier.
Ken Rideout
That's right.
Daniel Dart
Right. Or hate
And you would see that happen sometimes, man. And I remember seeing like young dudes come in and they're so vibrant and full of life and like 6 months later they have a swastika on their neck and you're like, "Holy shit." Like
Ken Rideout
They're so desperate for identity and acceptance.
Daniel Dart
Identity, acceptance, validation, all of those things. And I think the system is is built for that.
Ken Rideout
Yeah.
Daniel Dart
I think we're in charge of the environment from an institutional systemic place and whatever happens is because they allow it to happen or they want it to happen. And I think at that point just understanding the survival mechanisms and having grown up against so many different communities and groups, I think the main thing I wanted to avoid the best I could was politics.
Ken Rideout
Yeah. Yeah. Yeah. You know,
Daniel Dart
And some days are easier than others.
Ken Rideout
Yeah. Well, I think I feel silly because when I was asking again, I'm thinking of like a 13-year-old little kid like in like a a gang like from Greece and then I was like forgot like oh prison. Oh, okay. Now I what an idiot. But back to when you were a kid. So you're a kid homeless. Like you were involved in music. Like were you involved with music before you got arrested and and sent to the first time you did like real adult state time? No.
Daniel Dart
So I I had been involved in kind of like the punk rock community just because like um when I was homeless like think of like the young kids you'll see on the beach with like skateboards like raggly hair and dog and stuff.
Ken Rideout
You didn't have suspenders in Doc Martin boots.
Daniel Dart
No. No. I uh and so I kind of just was involved in the community. We go to punk shows, we do those. It wasn't until later on actually after a violation, I ended up getting getting arrested. And instead of doing like a six-year suspended sentence, I had to do a six-month like live-in kind of like work furlow treatment program. And I had a social worker there named Les Lazarus, who I always say his name. He passed away now, but he was an amazing dude. He um was the one who suggested I start a band.
Okay. Um and and kind of like on accident, he's like, "Yo, what do you want to do with your life?" And and realistically up till that point, and I was maybe 22 at the time, no one had ever asked me.
Ken Rideout
Yeah.
Daniel Dart
And I was like, "I I don't know." Because it was just like I think in the situation I was at, so much was built around survival. And I mean like very very core survival that we didn't really think like no one ever asked any of us. And I think in the six months um that I was in there, I think like of my 10 kind of closest friends, like five of them got killed. Other people got like arrested for life sentence. Like it was like so [ __ ] nuts and so volatile.
Uh my best friend, he got shot in the back multiple times and killed. And so Les, we ended up becoming buddies and he had asked and I was like, "I don't I don't know. I don't know what I'd want to do." And he was like, "Well, if I was a genie and you could be anything, what would you be?" And I was like, if I could be anything, I'd be a [ __ ] rock star,
You know, like cuz I was like a young arrogant kid. And he's like, then go start a band, you know? And it was that simple. But it was almost like permission. And I think I go back to the thing where it's not fearless, it's courageous. I think at that point in my life, like when you've lost everything, like there's nowhere to go but up. And then the more I started to think about it, I was like, okay, if I did want to start a band, how would I do it?
And so I started a band and and it went pretty fast, man.
Ken Rideout
So, okay. So, you start the band. How do you end up getting like your first real sentence?
Daniel Dart
So, I do the band. Before the band, I arrested I don't know, maybe five or six times.
Ken Rideout
When you get arrested, are you scared? Cuz you seem like like a smart guy. Like I the thought of getting like I got arrested once for fighting in Jacksonville, Florida with my buddies. I went down there was my buddy was playing pro hockey down there in East Coley. We got arrested and I'm like, "Fuck, we're going to jail." Like they arrested us and they're like they bring us to the city jail then they're like you guys are going to the county jail stripped down jumpsuits. I'm like I had already worked in a prison so I'm like dude we're [ __ ] going into the county jail like get ready like we're going into the g we're going in general population and they were like in you go soon as you walk in.
You know you got the little shaving kit and a black guy comes over. He's like hey let me get that toothpaste. And right away I was like you got the wrong [ __ ] I like like a crazy person. I was like you got the wrong [ __ ] person buddy. You ain't getting [ __ ] The guy who was with me was like, "Dude, are you crazy?" And I'm like, "If you give him that toothpaste, you know what you're going to be giving them next.
You don't want to know." And I was crazy.
Daniel Dart
Yeah. One of the things too, which you know, after prison, I ended up doing a lot of like policy work. One of the things that I always found surprising, especially when I went to the prison for the final time, is on every yard I went to, out of like 500 to a,000 people, I would know like 20 or 30.
Ken Rideout
Yeah, that's right.
Daniel Dart
Just from the system growing up. And the numbers, you think that's like staggering, you know? It's like 5% of the people you would know cuz you would like grown up in the same circles. And it's like, okay, well, in California, a state of like 40 million, the fact that I know 5% means that like there's probably some truth to the school to prison pipeline, right? Cuz clearly I don't know 2 million people in my phone. And I think just prison like if you got to fight, you you got to fight, you know?
I think it just it is what it is. I don't know how to say it otherwise. It's like I you know I don't want to like sound crazy violent on
No, I know exact [ __ ] goes down and like
You have to to escalate it. And I think sometimes I'll see people on Twitter especially in like tech and finance who have these like really outlandish positions around just war and this and I'm like bro like you clearly do not understand real violence. Yeah.
Right. like real violence. It's like there are no rules and things escalate so much. Like I was in some prison riots where like eight people got killed and beat to death. You know, it's like these aren't small guys. Like it just it it escalates so quickly.
And I think sometimes like even when I talk about risk because they're like, "Oh, you're a risk taker." I'm like, "Dude, starting a fund and failing like that's not risk, bro." Like to me, risk is like, "Let me throw the parachute out of the plane
And then you jump out and try and catch Like risk is something that potentially involves death.
Everything else, bro, is not risk. It's just that like you've lived such a cushioned life. That's right.
That you've been conditioned to one think you're tougher than you are.
Ken Rideout
Yeah, that's for sure.
Daniel Dart
And I think like do everything you can to avoid any type of discomfort.
Ken Rideout
Yeah.
Daniel Dart
Right. And I think the reality is is like in prison in those places like that's just not what it is. Like if [ __ ] goes down, [ __ ] goes down. And like it's about survival and it's that's that's just what it is. And I'm I'm a pretty big guy, you know? So I'm like 6'3, 250. Like I'm not a small guy either.
Ken Rideout
The thing you said about knowing people, that's what I always tell people when they're like, "Oh, this one's going to prison." I'm like, "Listen, if you're a white guy or a black guy, if you get arrested and you aren't a street person and you don't know the other people in your race, you're going to have a problem. It's going to be hard.
It's not about being racist.
You will align with your race whether you like it or not. And if you don't, you're gonna have a problem with both races. And I also think too, like when you said about like reception, right? Like when you get arrested and you go into intake and processing, like you know right away like I'm not saying like I belong there, but you know right away who belongs there and who doesn't like and so for me every time I showed up like you know I was like hey like like you just you know people and there's a different type of shared camaraderie and like you could tell who has
Daniel Dart
You know State Inc. and stuff like that. Like there's just stuff, you know, that I don't really think that you can you could fake. And I think that
Again back to the policy thing, I think that's where hard in California you always say like all roads lead to prison. And that's why it's so hard to reform is because once you've been there, you know that if you go back, whatever you do on the streets, you're going to have to answer for.
Ken Rideout
That's right.
Daniel Dart
And so that dynamic I think is very, very, very hard because it's just very, very, very real.
Yeah. And when I say real, like I think sometimes like you have these these things. We become an online society where people, you know, like I said on Twitter and this and that. Um, and I always hear people talk like, "Oh man, people were so much tougher. Like Normandy, we stormed that." And I'm like, "Yo, bro, like the fact that like we sent 8-year-old 18-year-old kids to go get shot." I'm like, "Fuck that shit." Like I don't have an 18-year-old son or daughter, but if I ever did, the last thing I would ever want them to do is like charge a [ __ ] beach in a hail of [ __ ] bullets.
And anybody that I think like promotes that
Ken Rideout
Yeah.
Daniel Dart
Again has clearly just never witnessed real violence.
Ken Rideout
Yeah. Well, I think that the people who did that, they didn't realize what they were getting into. But I think that the bravery and like I don't know. I feel so patriarch when I think, man, you're running out there. You can see people getting gunned down and you're like, I guess we all have to go. Let's go. The bravery that that no choice.
Daniel Dart
Yeah.
And I think that's like prison. What I always say in prison, like you're not getting out of here, bro, until they let you out.
Ken Rideout
Yeah.
Daniel Dart
And I remember when I first got there, I was talking about about an old friend who was a lifer. He was like, "Bro, your whole life on the outside, you need to forget that. That [ __ ] does not exist, bro."
Ken Rideout
Yeah.
Daniel Dart
Like that reality, like you got to cut it off. Like you live here now. This is your whole entire existence.
Ken Rideout
Even that is so intimidating and scary to me. Just like
Daniel Dart
It's [ __ ]
Ken Rideout
But to your point, but to your point, it's like it's like someone who's pregnant being like, I don't want to be pregnant. Okay. But you are.
You are.
Or you get drafted. Like I don't want to go to war. You're drafted. You're going.
Daniel Dart
You're drafted. You're going. I don't think it's about like, oh, I want to do this. It's like, yo, I have better chances. Like, I have to get through it. The sooner I get through it, the more I survive. And like, and it's just survival. And I think one, humans are super resilient. And and it's weird because even though you might have like mortal enemies in prison, I remember like I lost a friend while I was in there. I was just super sad. I remember crying and like someone from like who you would consider enemy came up like, "Bro, man, like just want to say like, you know, I'm sorry to hear that.
Like if you need anything, let me know." And I think there's like a human connection. And I think like we have to not lose sight of that. And I think that goes back to like the otherism or this or that. like, "Oh, let's just kill these people." Like, no, bro.
Ken Rideout
Well, that's the thing is I think that there are forces that are purposely dividing us and like promoting otherism right now more than ever before. Cuz
Even if you take someone who has like conservative views or liberal views
Outside of the extremists, right? Yeah.
Then most likely they're like, "Yeah, I agree on a lot of this stuff. I I let's just agree to disagree. I'll never see it that way, but I don't have any problem with you. I have a lot of friends that I disagree with politically, but not like I hate them or despise them or but if you listen to the news, you would think that we're mortal enemies in that like one party is trying to destroy the other all the time. But before we I I want to get more into like the experience of getting in there and like the reality of when you hit prison, but what talk about the charges because I know you had him overturned.
Daniel Dart
What were you accused of?
Ken Rideout
What did you commit?
Daniel Dart
What really there's all sorts of stuff, but really the the prison thing is like carjack, kidnap, um, which really stems down to moving someone in a vehicle over 100 ft.
Ken Rideout
Okay.
Daniel Dart
You know,
Ken Rideout
Cuz they make the the charges sound probably a lot worse than what the incident was.
Daniel Dart
Yeah. Yeah. I mean, it it sounds nuts. I think, you know, when I first got arrested, everybody was like, "Hey, there's no way you're going to go to prison." And they had arrested a bunch of of my friends for different gang stuff. And they were like, "Tell us about them. Tell us about this." All these things. And I'm like, "Yo, honestly, I don't know. Like, I'd love to tell you. Like, I'm not trying to be, you know, Billy Bass, but you know, who, what, where, why, and when has a bump on their head, right?
So, I am not going to ask questions. Do I know that like he probably shouldn't be driving a Ferrari or Lamborghini?" Yeah. But I I don't know. And then as I got more into it, it was one of those things where it was like, "Hey, it just looks bad. Like, you're definitely gang affiliated. you're definitely like, you know, around people who are doing bad things, which to me, and we'll kind of I'm going to jump back to that. So, we'll get back to the the broader affiliation, but at that time then my lawyer was like, "Hey, man, like this doesn't look good." Like, you're you're going to prison like for sure.
Ken Rideout
The other one quick thing I'll say is when they're like, "Who did this? Who did that?" You almost want to say to the guy like, "You realize like I've been arrested before. I'm a you think I'm affiliated with these people. If I tell you anything, guess what's going to say on my paperwork when I get to prison? Yeah. And guess who's going to be dead? Me.
Daniel Dart
So,
I think even then I was just like I was like, "Yo, man, I'm not involved." Like,
You know, they always say if nobody talks, everybody walks. You know, but
Ken Rideout
But that never happened.
Daniel Dart
It doesn't happen, you know? But I think that the thing about it is I just felt like, yo, clearly I'm actually not involved. So,
You know, I thought it would run its course. There was no violence, like all this stuff. Then I ended up my first offer. It's weird. I I I feel like I should remember this. This is like how how great the brain is dealing with trauma was like 150 years.
Ken Rideout
The fact that they would even offer someone that is like what's my downside to taking the trial?
Daniel Dart
No, this [ __ ] woman uh I [ __ ] wish I remember her name. She said uh but at least it's not a life sentence. You can get conjugal visits. If it's a life sentence, you can't get conjugal visits. And I have to say a very very powerful moment is
So you're in there and you have 72 hours to get arraigned in California. Yeah.
And there's like big groups and they get like 200 300 people to get arraigned and like you know people got DUIs or domestics or all this [ __ ] and so everyone's in there and you kind of get to know the people like I'm trying your charges.
Okay. So I'm telling you about it. So it's at the end of the day you know everybody like some people came back oh I got time served. I got this you know and it's at the end of the day and they come in they're like they call your name. Uh I said yeah what's up? like, okay, well, you know, this is serious and you know, you got this this this and your uh it's called uh predisposition that you're leading is uh 150 years and the whole room just goes [ __ ] quiet, right?
Cuz they're like, "Holy shit." And I'm like, "Fuck." Like, and and I'm like, "Yo, well, I'm not going to take that shit." You know? And then the whole room is just super quiet cuz they're like, "Holy shit." They look at you just with different eyes like yo this [ __ ] and what we always say is football numbers, right? Like cuz we always say football numbers like 88 on a jersey or something like
And then you like sit there and you're like okay this is going to be going to be a real thing and I ended up fighting it in county for about a year.
Ken Rideout
And by the way just to clarif clarify one thing when you say you fighting in county meaning you haven't been charged and anytime you're not anytime you haven't been convicted so when you're not convicted in the in US court you're innocent until proven guilty. So theoretically, this is why with this bill reform and people like have a big problem with it. It's like to a certain extent you're like, I haven't been convicted yet, so I'm I'm innocent in the eyes of the court, so why am I being held in jail?
Which is and obviously if they've got you dead to right, they'll be like, yeah, the bell's 10 million or no bail because they might have you on, but they know you're guilty. Hey,
There's pretty good evidence that you're guilty or you don't have two nickels to rub together and your bill's 10,000 and you're going to sit in in county jail until your trial comes up. So, it's crazy cuz you could have one guy who's in there facing life prison for murder and a guy who got arrested for his fifth drunk driving-in who's on 10,000 bail and doesn't have two nickels to rub together and now they're cellmates and you're like, "This guy's going to jail for murder for the rest of his life and this guy's going to get out in like six months."
Daniel Dart
Yeah.
So, it's really Yeah. So LA County Jail is [ __ ] crazy
Ken Rideout
Crazy
Daniel Dart
Crazy
Ken Rideout
One of the most dangerous places probably in the whole country right
Daniel Dart
I think probably it's it's very very very very volatile
Ken Rideout
That Rikers
Daniel Dart
And yeah I I never went to Rikers thank goodness don't ever want to go but um yeah I I fought it in there for about a year and you you have different numbers on your wristband and they would call them and every time like new people came in they called to be like holy [ __ ] you've been here [ __ ] a year and you're like yeah and so I ended up um in the long run ended up pleading out to the deal and and pleading guilty in order to fight it in appeals courts.
Ken Rideout
Yep.
Daniel Dart
And so there's a bunch of stuff that that kind of you have to clear up. So the initial court is a jury of your peers.
Once you go to appeals court, it's case law.
Ken Rideout
Yep.
Daniel Dart
And it's it's judges. And so that's much better because a lot of times
And this is why like it the most famous of cases is like Thurgood Marshall when he used to do different racial stuff in the south. He's like, "Yo, I want to fight case law because like was this by the rule of the law
Happened?" And so for me, I ended up, you know, pleading out to that. I remember I I end up getting to prison
Ken Rideout
Like when you hit the yard, not processing.
Daniel Dart
So in in California, you do processing for like 3 months.
Yep. And then you hit the yard.
Ken Rideout
And where did you go?
Daniel Dart
So my first one I went to Delano. That's where I was processed. Then I went to California Men's Colony West. And then from the Men's Colony I went out of state. So I was one of the guys. Do you remember in California in like 20101 there was overcrowding. So they sold 10,000 of our contracts. And so I went to Arizona and Oklahoma.
Ken Rideout
That's crazy. Was it better or worse?
Daniel Dart
Uh both in some aspects. Like it was better for, you know, you had three hot meals a day, which was nice. Um, you could use an Xbox, which was nice.
Ken Rideout
What?
Daniel Dart
Um, and they they had
Ken Rideout
An Xbox.
Daniel Dart
Yeah. And they had dental care.
Ken Rideout
Come on.
I've never heard of a video game in prison.
Daniel Dart
Yes. A lot of them have them, but in California, they don't. Um, but in out of state for the private prisons, you could have one.
Like you can't use the internet, but you could just play games. And it's crazy. And then but there was a lot of bad things like one like when [ __ ] went down like it went down a hundred times worse because I was a threat to guards like they're like yo man like I ain't getting involved like like I was at one prison where the prisoners took it over like eight days the national guard had to come get it back and [ __ ] So um
Ken Rideout
In Kelly what were the really bad ones? Pelican Bay Victorville.
Daniel Dart
So Pelican Bay I would say High Desert Victorville I mean
Ken Rideout
Very very gang
Daniel Dart
I think there they all were. When I was at CMC West, they integrated the yard with with um Norteños, and that [ __ ] was [ __ ] was nuts.
Ken Rideout
Norteños are like the northern Mexicans. And what were the southernos?
Sureños. Yeah.
Daniel Dart
Yeah. And then you have the Pis, right, which are like the Mexican.
Then you have the Bulldogs, which are the Fresno Mexicans.
Ken Rideout
What about Isn't it Mexican mafia, too?
Daniel Dart
Again, I don't know, but I think they're I think they're part of the Sureños. It's been a long time, so I don't I don't know. I don't want to speak on it.
So crazy. And then what were the white gangs? You you know you had the white dudes which are just like pecker woods, you know, and then you had the skin heads
Which I I think people don't realize a lot of times they they actually don't run together.
Ken Rideout
All right. So you go out of state. How was Arizona? Was it Did they have air conditioning?
Daniel Dart
So Arizona was kind of [ __ ] up because I was in a a food strike there which is crazy, you know, or a hunger strike. So it was actually the biggest hunger strike in American history. We made the economist. I remember reading about it like a month later. It had started. So there's like levels. There's level one, two, three, and four. Pelican Bay is like level four, but anybody on level three and four had to
Had to hunger strike
Ken Rideout
According to the other inmates.
Daniel Dart
Yeah. Yeah. Yeah. Like you
You didn't have to, but like you know, you had to.
Ken Rideout
Yeah. You had to.
Daniel Dart
And I think level three, if I remember, we had to do it for 5 days and that was like a [ __ ] But then all of a sudden, you know, you get it on your you get extra time, you know, cuz like if you
Ken Rideout
Disruption.
Daniel Dart
Yeah. Like I think if you deny your your food tray more than three I can't remember.
Yeah, I got you. you know, but I'm like trying to fight my appeal and all this [ __ ] I'm like, [ __ ] And then there's like a riot, so I end up catching all these like extra 30 days, 60 days and that [ __ ] you know, you're like, it is what it is. But, you know, the DA tries to use that as like, oh, you're a problem inmate and stuff. Even though they know whole well that like that's just not true. It's just that's the
The politics you kind of live and die by. So, I was in Arizona for a few months, then Oklahoma for for about a year, then I came back for my appeal, and then, you know, they sent me back. And that I think probably the worst day of my life was you're on this bus for like, I don't know, 24, 36 hours, and you're handcuffed. You know, you're shackled at your ankles, your waist, and um your hands. And you know, they have like a little black box you put your hands in,
And then you can't move, and you can't stand up or nothing. And you know, the guards would have shotguns and they'd be like, "Hey, you know, if you talk, we'll [ __ ] kill you." You know, and and like, but crazier than that, like you're just like, "Fuck." And you know, you can't use the bathroom or you can't do any of that stuff.
Ken Rideout
So, hypothetically, like, what if you really have to go? You just
Daniel Dart
I mean, I I you know, no one had to hypothetically go. I I think I don't [ __ ] know. They probably guards would [ __ ] you up. I don't know.
Ken Rideout
People listening, they probably think, "Oh, that's an exaggeration." I can tell you firsthand, like people are vicious. Guards. Guards are no better than the inmates for the most part.
Daniel Dart
It's not. Yes.
Ken Rideout
They're like their own gang,
Daniel Dart
Dude. It was I mean, it was crazy. So, LA County, I think, you know, they caught that they had gangs and [ __ ] Lee Baka and then he pretended he had dementia, right, to like get out of it.
Ken Rideout
They had gangs at internal gangs in the LAPD. Yeah.
That's like famous cases.
I mean, that's like Trading Days about like that's a true story.
That's a very true story. I know a girl who was a writer on one of those um a TV show in LA. She was my neighbor in the Palisades and she's like telling me about it. She's like, "No, no, I covered the whole thing." She's like, "They were legitimate gang members in LAPD that were like doing training day [ __ ] like robbing and stealing and killing."
Daniel Dart
Yeah.
[ __ ] crazy.
Ken Rideout
Crazy.
So, when you were there, did you know like you knew you were intelligent? Did you think like, okay, once I get here, I'm going to just study the law myself, write my own appeal, and like did you think you had a good understanding of how you could return it?
Daniel Dart
I I think, you know, cuz I ended up like speaking and representing myself at appeal. I think at that point,
Ken Rideout
Hold on. How did you know that you could do that just from research?
Daniel Dart
So, the whole time I kind of trusted the system,
Right? Yeah. I know it sounds laughable, but at the time I had trusted the system and I thought like, hey, there's there's no way and this like conspiracy theory, but I feel like I don't know like my lawyer pawned me off for some other case like or something like made a deal like, oh, I'll give you this if you take this. Then I had a lawyer that helped file my appeal. But then when I came back, which would file, so I initially filed, I think it was penal code 1170 with the writ for habeas corpus that I have been illegally sentenced.
And so there was certain things that I did to get things on the record. And one of them was when I plead guilty to the kidnap carjack and assault, um, what type of time credit would I get, right? And so the time credit is for the time that you served in county jail waiting trial. So if you do a year in county jail waiting for your trial and you get sentenced for two years, well you got a year of credit for time served waiting trial.
So it could be that but also in states. So in California state there's three different times you can do. So you can have 85% for violent crimes. You can have 50% for regular things. And then if you're in certain places, you could get 33, which means that like
One day, 2 days time credit, one day, one day or like one day and.5.
Ken Rideout
Yep.
Daniel Dart
And so under the the crime that I had been convicted of, I would have had to do 85% of my time.
Ken Rideout
Got it.
Daniel Dart
But when I was in open court and I was going back and forth, I was like, hey, you know, because there's no violence in my case, then I should actually get credit for one for one, right? And the judge was like, "Yeah, I agree." And I'm like, "Okay, so you state in open court that, you know, there's no violence. I'm good. One for one." She's like, "Yes, I agree to that. Cool." The DA is like, "Yes, I agree to that." So then if there was no violence, how could I have been convicted of a violent crime, right?
Ken Rideout
So this is in hindsight. So you you go through your sentencing, you've already made this, you've you've argued the fact that there's no violence. They've agreed. Now you're sentenced. So you're thinking, "Oh, I got them." And so then I file to go back
Knowing that that's what you're going to file under.
Daniel Dart
Yeah. Yeah. Okay. And so the way I would say it is
Imagine like you're walking down the street and you see like six big guys down an alley and like you're scared.
Well, like are you scared because they had done something or are you scared because like in your mind six and so to me like the situation where I was in pretty much what happened is ex-girlfriend she had stopped the car. I stopped the car. I admitted to stopping the car over 1,000 ft. So technically, I admitted to breaking the law, but the spirit of the law is what the magistrate says is like, well, I know it says 100 ft, but the spirit of the law is like not like, oh, stop the car takes 1,000 ft.
Ken Rideout
Yeah.
Daniel Dart
Like clearly you're on the freeway, so like I can't stop the car.
Ken Rideout
Yeah.
Daniel Dart
Like so the spirit of the law he did not break, right? the and so like there was a technicality and so when I went back and I talked to the appeals judge she agreed. She's like no I agree like based on the spirit of the law like you were incorrectly charged and sentenced. There's two things I can do to you today. One I can like overturn everything but the state has the ability to refile charges. or two, I can you could wave your constitutional right and I can like lower everything to the lowest mandatory minimum and then you could potentially like go home soon.
Now, I couldn't go home that day because I had extra time for the riot, extra time for the hunger strike, all of those things that that I had to do that were on the extension.
Ken Rideout
Thanks, fellas.
Daniel Dart
Thanks, fellas. Yeah. Yeah. Yeah. And so at that time I I had asked her I said well you know
Ken Rideout
And you're having a conversation with the judge yourself because you're represent and and and is there a prosecutor or someone
Daniel Dart
There's there's a prosecutor there that tried to rebut me and the judge was like yo shut the [ __ ] up.
Ken Rideout
You don't have a leg to stand on.
Daniel Dart
Like she was like it actually felt really good cuz she's like yo if you weren't doing like shady [ __ ] [ __ ] we wouldn't be here to begin with. So like I I don't want to hear anything. It's crazy to think you got the honest judge in a [ __ ] state court.
I think the thing about with judges is I think the thing is like I think more of them are better than than worse, but they're so tied because of mandatory sentencing guidelines.
Ken Rideout
Yeah. Yeah. Yeah. Yeah.
Daniel Dart
And so she had told me she's like, "This is all I could do to you." She had said, "I wish I could send you home today. I can't."
Ken Rideout
So when she says choice one, I can overturn it, but they can refile. Meaning even if I overturn it, you're not leaving. They're going to they're going to hold you until they decide what they want to do. So, if they overturn it, she's like, I had asked her, "Well, what would happen?" And she's like, "Well, I I don't know. You would get rearrested or whatever and it would go back to the county, so I wouldn't be in charge of it."
Daniel Dart
And I was like, "What would my bail be? What do you think?" And she's like, "Candidly like, I don't know. I would expect that you would have no bail, right?
Cuz they're not going to be happy." I actually was like, "Hey, could I take a beat and like, you know, like call a friend like me?" So, I ended up like cuz I was just like, "Wow, this is like because at that point I wanted to refight it." You know, I was like, as I could imagine, resentful. And I ended up calling a friend of mine named Ian. And I'm like, "What should I do?" And Ian's like, "Bro, you've been gone three years, bro. Like, just plead guilty." Like, what the [ __ ] man?
Yeah. And even saying it out loud, like it's hard because like time stopped. So like my last day of reality was like the day I got arrested and I just remember him saying that like, "Bro, you've been gone three years."
Ken Rideout
If she resentences you to all the minimums, would you be like on like
Daniel Dart
So then I went like, "Yeah, I'll be at the finish line." And so I ended up, you know, pleading out to that and then they
You took choice B. I took choice B. Okay. And then Yeah. Then I got out uh a few months later and that [ __ ] was nuts, too. You know, I always say the worst day of my life probably on that bus. The best of my life I always always talk to my partner Annie. I'm like, we get married. I have six kids. I still think the best day of my life is me getting out of prison. I don't know if you're going to top I don't know if you're going to top that.
You know, it's pretty good. It's like
Ken Rideout
So, wait a minute. So, okay. So, what happens on the day you're released?
Daniel Dart
So, at that point, I end up winning my appeal. it all gets granted and and all those things, you know, the initial stuff gets overturned and but I didn't know exactly when my release date would be. There was like three different options. And so I ended up getting transferred to CRC, which is California. What is it? CRC. It's in it's in uh Norco and it's it's kind of famous cuz it's Hotel California.
Yeah. you know. So, I'm there and it was like that was [ __ ] crazy because it was like a low-level yard like the lowest level yard I've been on and you know they called it the roll up or the spliff because so many people would like roll up to PC.
Ken Rideout
Yeah. Oh, so it was like a kind of a PC yard because it was low. It was like low low level. So, it was still general population, but when we got there, you know, the guards from where we came from was like, "Hey guys, you know, like you're going to have to change your program a little bit and [ __ ] like that because they put in like PC guys there because they think they'll be safe here because guys like you who they might not be safe around or the people that you affiliated with
Because they might be sex offenders, but you're on short term. You're on short time. You might be out in 3 months, so you're not going to run the risk of like killing a sex offender." So it it's weird. They don't have PC people there, but like what what turns out is it's usually like the dope fiends and [ __ ] that become PC.
Daniel Dart
I got you.
Right. Cuz they're all strung out because like there's very little repercussions
Ken Rideout
And so politics are not as stringent.
Yeah.
Daniel Dart
You know, like people share sinks and like [ __ ] that like you would just not do
At a high level yard.
Ken Rideout
And for people that don't know, sharing sinks mean races sharing sinks. In a high level yard, no one's there's no like you're not sharing anything,
Daniel Dart
Right? And and the thing about it too is like at the low level yards, they even have full length toothbrushes. Like at the yards I was at, when you get a toothbrush, they cut it so it's really short. Like you have a real toothbrush head.
Ken Rideout
So you can't sharpen it into
Daniel Dart
You can't sharpen it into like, you know,
Ken Rideout
So crazy to think that there's like this whole level of society that most people thankfully will never know, but when you know it, you're like you can't it's like you can't unsee it. You're like unse. And even with that, you're like, why would they cut the toothpaste? And and to people who know, you're like, "Well, of course they would. You want someone to stick that in your neck?"
Daniel Dart
You know what I mean? It's crazy,
Dude. It's crazy. And so I get there and you know, people tell you like even when you come on to, you know, whatever dorm you're in, they even tell you like whoever's got the dorm or the building will tell you like, "Hey guys, you know, like we we run things, relax here." Cuz they don't know. Like a lot of times they're just as worried because they're like, "Fuck, this dude's going to cause [ __ ] kick off a riot."
Ken Rideout
And by the way, I just I feel like I should clarify people when he says who has the yard, meaning each race essentially has a leader of the dorm.
And when a new guy, let's say a new white guy comes in, they'll be like, "Hey, I'm in like I'm in charge here." The shot caller, here's what's going on. We're chill here. I know you're coming from level four. We're not like killing people for using our sink. It's kind of like we all want to get out of here.
Daniel Dart
Yeah. Like you'll see like, you know, white guys sit on black beds or black guys sit on white beds and like you'll see a lot of stuff that like you would just never
Ken Rideout
Yeah.
Daniel Dart
See. And it does like the first week or two you're like looking around like what the [ __ ] And so then you're there and uh and so I end up, you know, and it's crazy cuz actually in my dorm um there was a dude that I had known, we had grown grown up together that I'd known forever.
And so it was like there was a bunch of people I knew there who were they're all there just like fuckups, you know, got busted,
Ken Rideout
You know, smoking dope, something
Daniel Dart
And um and I was there for a few months and I end up getting released. But the day I got released, it's the best day. It's like the best feeling. here like you could finally breathe again cuz I think you know your like your adrenaline levels are in prison like you know say if like 10 is like a [ __ ] allout riot one is like chilling at home when you're in prison I don't feel like they ever go below five
So you're at all times really just kind of on your toes and I don't even think it's like it's a conscious thing I think subconsciously you just know like you're [ __ ] in it.
Ken Rideout
Well, you're a dude and you're in there with a people who are not good people and you're sleeping in a dorm like on a bunk bed next to another freaking guy who could be a degenerate like drug addict
Daniel Dart
all sorts of like mental disability and like so you know they call them JATs, right?
Which is like the J category where like you know you you're not all there.
Yeah. And you can't get away from these people. You're you're in a
Ken Rideout
Like you see a guy on a subway where you're like yo something ain't right. I'm going to go to the other thing. Well, in prison like that guy sleeps in the bed next to you. You ain't going anywhere. And it's so that's what you mean about just heightened anxiety where you're like, "Yo, I'm sleeping like with a shank like next to me." Like the things that I would see in there were just
Crazy. And I when I went when I started working there at 18, I graduated high school. A week later, I'm in the prison and first day I walked in, there was big Irish guy, uh, Barry Hilts from the projects near where I grew up. And I he sees me and it's like all of these things are hard for someone who didn't grow up like this to understand. But he comes running over and picks me up on his shoulder like a fireman's carry. I'm in my guard uniform and he starts running with me on the on the track and I'm like, "Dude, put me down." And my first instinct is not like I'm going to get him in trouble.
My first instinct is the other guards are watching me, dude. Put me down. I don't want them to think I'm like congregate like uh hanging with the inmates. And uh
He was like, "No, no, no." And he put me down. He goes, "Don't worry about it. I'm letting everyone else know here that you're all right like the other inmates. And that's literally what he did. And then the other I mean the white inmates, the other the black guys and the Hispanics were like, "Fuck this guy."
First day I'm going down the tier and it was steel doors and a little uh window with bars and I'm looking in looking in this gigantic uh Puerto Rican kid, huge bodybuilder, tattoos everywhere. He jumps up from underneath the window. Dude, it scared the [ __ ] out of me. My flashlight went flying. And I was like, "Oh." Of course, then I'm like, "Oh my god, I got a safe face." I'm like, "I'm going to get you." And then I came back like with a spray bottle, like sprayed him with water, clowning on just to like be like, "Yo."
Daniel Dart
Yeah.
Ken Rideout
Scared the [ __ ] out of me.
Daniel Dart
Yeah. You You would see every every few months, man, you would see certain guards where like you knew it was going to end up bad. And there were certain times on yards where guards would be treating inmates poorly and like certain people would step to they had a thing called a MACR rep which is like almost like the prisons union that would talk to the guard.
Ken Rideout
Yeah.
Daniel Dart
What it meant was uh Mexicans uh Africans and Caucasians.
Yeah. you know, they didn't those are the only ones that, you know, apparently apparently it's not very woke in in prison, but uh and they would step pull a pull a guard like a sergeant and be like, "Hey, man, like you need to you need to to get this this guard off the unit."
Ken Rideout
People don't understand that.
Daniel Dart
And every once in a while they'd be like, "Nah, like we ain't going to listen to you." And [ __ ] and like clockwork, like it would it would be [ __ ] bad. I remember like seeing a few guards like where you're just like, "Holy shit."
Ken Rideout
You know, and you're just like, "Okay." Like people don't understand. Like they like think it's like Shaw shank where like you're walking with a bar stick banging it on the bar. It's like you violate an inmate or disrespect an inmate as a guard,
They will punch you in the face. There was a young kid who was like young black kid. He was like, "If you didn't have that badge on, I punch you right in your face." And I was like, "Oh, really?" I went to take like I was like, you know, "Oh, I'm not even going to test me." "Oh, really?" I go to touch the badge, boom, punch me right in my face. Broke my nose. I was like, "You, you know, and then of course we bundled him and got down to the shoe and beat the [ __ ] out of him." But I was like, "This guy was like, he's crazy." Another time guy, a guy came running out of his cell, he had a uh, you know, like an electrical stinger that you put in the hot water, the heating coil.
Yeah. He had straightened it out into like an ice pick and a white kid had gone into his cell, black guy, and smashed his head in with a cribage board while he was sleeping. Crazy, right? He comes running out and it was a white kid that I knew. And I think he thought that I had something to do with it, which I didn't. He comes running towards me with this thing and another guy jumps in between us and the guy starts swinging wildly and stabs him right through the cheek.
Knocked his tooth out and then we tackled him down. But I was like, I got to get out of here. That was when I was like kind of not studying as hard as I should, thinking maybe I'll take this job for the rest of my life, civil service job. And after that, I was like, dude, I have got to start paying attention in school. This is not the way I want to live.
Daniel Dart
Yeah. I think uh I had seen a few guards too where you'd know they get like warnings from the inmates like hey this doesn't and I I remember one I can't remember guard I remember it was a it was a huge big brother with dreadlocks and like you know he got the call he's like I'll take this you know and it was like it was a wrap because the thing about it too you can't move quickly so if you catch a guard or somebody at the wrong time like they got to go through doors they like
To get to you it may take even at the fastest time 60 seconds, which like 60 seconds when someone's [ __ ] you up, that's huge. Like
Ken Rideout
That's a [ __ ]
Third of a boxing round.
Daniel Dart
But I think the thing about it is it's like it's a it's what I always say is like in when people talk about like prison fights or something, the difference in county like when you see two men fighting that are really like trying to hurt you. Yeah.
Like again, it's like you don't understand like it's not a bar fight.
Ken Rideout
That's right.
Daniel Dart
Like this is like yo
Ken Rideout
To the death.
Daniel Dart
Yeah. Like it's literally like when you're going in that fight, you might die.
Ken Rideout
Yeah.
Daniel Dart
And so I think the level of violence is escalated by the level of fear and the consequences. And so bad things bad things happen.
Ken Rideout
It's scary and it's traumatizing when you see two guys fighting like that. Like I for the longest time had like terrible
Daniel Dart
terrible dreams where I was like it's traumatizing, man. Because I I think the thing about it is like you're put in these situations. And I think sometimes when I think about it on the streets with like young kids in Chicago, the minute escalation happens,
Ken Rideout
It stays at the escalated version. That's right.
Daniel Dart
Because you have to respond in time.
Ken Rideout
Yep.
Daniel Dart
What am I doing here?
Ken Rideout
Like I need to get out and turn my life around. And how do you start thinking about LSE?
Daniel Dart
So I I think the one thing that I realized is, you know, people say you're the median value of your five closest friends or like show me who your friends are and I'll show you who you are. I don't think that really ever clicked in my head until this because even though, you know, I'm like, "Hey, I never should have gone to prison in the first place." I was hanging out with people up to no good, I just didn't think it impacted me.
Ken Rideout
Yeah.
Daniel Dart
Right. Like I thought like I'm not involved, so like it doesn't matter.
Now I'm like, yo, whether you're involved or not, the fact that you're around those people, like you're going to deal with the good or the bad. And so I think the first thing going out of prison, the biggest thing was like, yo, no matter what, like even if like I have to scrub toilets forever, like I'm never going back to prison. Like I'm never going to put myself in that situation. Like no matter what, like that's the baseline. And then on the other side of that was like, okay, that who you associate with can work with you either way.
Y
And so the goal was like, okay, all I want to do from now on is try to surround myself with the best people I possibly.
Ken Rideout
And how do you even think about going about that? Because up till now, you're like a gang member associating with like
Daniel Dart
Incrementally really like so the first thing was like, hey, what could I do to put income and just survive? My first job out was I changed sheets at Airbnbs. I was a maid.
Yep. And then, you know, I I I'm a sober guy, so I would go to meetings and all that. And then it was like that was saying like just find the winners.
Ken Rideout
Yep.
Daniel Dart
And anybody I thought was like a winner, doing really good, I would just be like, "Yo, man, I just want to be your friend. Like, can we
Can we hang out? Like, what could I do to just
Be around that?" Because I also think that
Humans are just super medicic, right? like peer pressure is unavoidable. And so to me, I wanted to surround myself with really good people also in a way where I didn't want to let them down.
Ken Rideout
Yeah.
Daniel Dart
And so over time, I just continued on that path like, hey, how can I find really good people? And I didn't have the answer to everything and I still don't, but I have the trajectory. And so over time, I'm just like, "Hey, I want to surround myself with the best people doing the best things." And and I I say it a lot, like if you surround yourself with good people doing good things, you will ev inevitably end up in good places.
Ken Rideout
But how do you even meet a good person like that that that can direct you to start to think about LSE when you're like changing sheets at a hotel?
Daniel Dart
So initially, you know, I ended up going back to the the music industry. I ended up from from changing sheets. I ended up working um on the management team uh with Weezer. So I ended up managing Brian Bell.
He had a side project that that I was helping be in charge of called the relationship.
And through that, I still knew that wasn't my thing. And then I ended up meeting a woman named Danielle actually at a birthday party. And I was just thinking about her recently when I was working on my book project I was talking about.
And she was doing her PhD on like criminal justice stuff at UCLA. and she's like, "Yo, we have a criminal justice working group. Like, you should get involved." And I ended up getting involved in that. And as I got more involved in like criminal justice and policy and and different kind of law making and that, there was just a lot of really good people, really smart, doing really good things. And and not only that, like things bigger than themselves, like where it's like, yo, I'm trying to change the system.
And I went from working with artists And I was working with like Santana and Seal and Jurassic 5. But over time, like this this version of pursuing something bigger than me was super appealing.
And then as I got more into the social policy place, that led me to, you know, doing things with the Obama administration, eventually connecting with people at the World Bank and starting to work overseas in Africa, the Middle East, and continuing that path like just yo, where are the winners at? It was through that journey and kind of that escalation on the good side that I ended up learning about venture and just academia.
I ended up meeting this guy at a friend's like going away party. She worked for the World Bank. Her name was Selene and her boss was this guy named Gunther Sha Linter who at the time was the executive director at the board of the World Bank. and we had met and just had this really great conversation about all sorts of different like global kind of issues and politics and he ended up becoming a friend and a mentor. He was actually the first person that wrote a recommendation for me to go to LSE.
Ken Rideout
Where did the LSE idea even come from? Just from being around the World Bank people and hearing about LSE.
Daniel Dart
Yeah. So I ended up, you know, ended up going from really LA to DC, working on a bunch of national campaigns for social impact, public policy, working with veterans and, you know, and entertainment companies, eventually Save the Children Global. I I I caught my first big break on like the kind of international policy thing. I got a job as the first kind of outside consultant for the Bezos family foundation.
Ken Rideout
Okay.
Daniel Dart
And that was like radically changed my thing. And I remember when we were talking about it, I had talked to like the program director there. And it was funny cuz Mike Bezos Jeff dad was like the contract person. I remember being like, "Yo, you know, I just got out of prison, right?" And they were like, "No, we didn't know that." I'm like, "Well, I want to tell you because like you guys are a big name." And at at the time, I didn't know the term was headline risk.
Ken Rideout
Yeah.
Daniel Dart
But I was like, "Hey, I just don't want to get you guys to think I was like lying or something." And I'll never forget it, man. And like it was like yesterday they wrote back, "Okay, well are you going to go back to prison?" I was like, "No, I'm not." They're like, "Can you do the work?" Like, "If we give you this job, can you are you capable?" And I said, "Absolutely." And I'll never forget this. And I don't even think they remember it. I don't even think, you know, Mike Bezos remember, well, we're a new foundation.
So if you take a chance on us, we'll take a chance on you. that like catapulted me because now I had this huge name and like really good pay and it was like the first time post prison where I felt like I might actually have a career that I enjoy and I started working on a project for workforce development in Nicaragua and Indonesia and then that ended up leading to a project in Algeria which led to more economic development thing stuff and that's when I started learning about venture and building economic kind of like stability and investment and bottom up and I was like blown away.
And as I was researching it, I started researching academic papers and like following academic conferences and like watching speeches on YouTube and eventually I'm like, yo, I want to write my own academic paper. I want to write my own thing. And I had no idea what the [ __ ] I was doing, right?
And so I ended up writing this [ __ ] It was like so bad. But what you what I didn't realize at the time is at a lot of academic conferences, if you submit it and they deny it, they'll write notes on it.
Okay? So they'll be like, "Yo, this sucks because of X, Y, and Z."
Ken Rideout
Yeah.
Daniel Dart
So I get those notes back. I like work on it and and then along the way I started emailing like these famous economists like one was Josh Angrist who won the Nobel Prize and is a professor at MIT and and we had become buddies like he even when I got accepted he's like hell [ __ ] yeah. And I just kind of would send this. I would ask for notes. And then as I like started to think about academia like hey maybe this is a chance.
My friend Johan who works at the World Bank as well um he was like bro you should just try to do a masters and with LSE LSE you know I think MIT is a bigger brand but as far as economics like 33% of the the Nobel prizes are from LS.
Ken Rideout
Yeah. Yeah. For sure.
Daniel Dart
So as far as finance and theory I I think it's the best in the world.
Ken Rideout
And has anyone ever gone to LSE without an undergrad degree? Not that I know of. Um,
So funny to even think about.
Daniel Dart
Yeah, it's so funny. And at the same time, Gunther went to LSE. That's where he had done his PhD. And even now, like I look up to him so much. Like he's like someone I want to aspire to be like. And so I just thought like that's the pinnacle, right? And and there was a few other things. There's more people to World Bank, IMF, and Goldman Sachs from LSE than any other university. And at that point, I knew I was smart, but I also knew that in order for me to go from where I was to where I wanted to be, which was eventually running my own, you know, investment and venture firm.
Not only did I have to prove I was good, but I needed to prove I was good by the rules and constraints that other people had. And not only did I have to do it, but I had to beat them at their own game.
Ken Rideout
Yeah.
Daniel Dart
And so then I was like, "Okay, I'm going to go to LSE." And not only to go to LSE, but I'm going to do two masters at the same time. I was also the first and only student I think ever to do two masters at the same time. And it's weird to this day I still have two different alumni codes and all that cuz they never figured out how to merge them.
Ken Rideout
Yeah.
Daniel Dart
Because even the system was like holy [ __ ] Like we've we've had people do undergrad and a masters and a PhD. But we've never had someone in two programs at the same time and they never figured out how to do it.
Ken Rideout
And while this is happening, are you living in London?
Daniel Dart
I'm living in London initially.
Ken Rideout
How soon after you got out of prison is this going down? This is about 6 years after.
Did you ever have moments where you're like, "What the f?" I was like sleeping next to like Peckerwoods and now I'm like rubbing shoulders with like aristocrats at LSE.
Daniel Dart
Dude, it was it was nuts. So, so initially when I I was living in Saudi Arabia at the time, I built the thing. So,
Ken Rideout
By the way, how are you once you when you've been convicted? Was your crime complet was your was your conviction completely overturned?
Daniel Dart
No. No. No. So, how do you get a passport? like how do you get the travel?
So, you can get a passport. Uh
Ken Rideout
But countries won't let you in if you're a convicted.
Daniel Dart
Certain countries won't. And it's weird like and I want to give a shout out to to Saudi Arabia
Ken Rideout
Cuz that would be one of the countries I would think wouldn't let you in.
Daniel Dart
So, I actually I was flying through Saudi on the way to Abu Dhabi for a work thing last year. And I honestly think Saudi Arabia gave me my life back.
Words. Words that have probably never been said. And so it was weird because as I started working in Algeria in the Middle East, I worked in Gaza, I worked in Egypt, I worked in Ghana, and this is all for nonprofits.
This is like for like UN, African Development Bank, Mercy Corps, Oxan.
Ken Rideout
So finance related jobs in these under
Daniel Dart
International develop related jobs which a lot of times had an economic angle and a financial angle but much more like economic policy.
Got it. And I knew I wanted to transfer to the investment side, but Saudi was the first place I went to where they just didn't have prison stigma. So like their whole thing like on a cultural level was like, "Yo, you've done your time. Like you've done your time."
Ken Rideout
Yeah.
Daniel Dart
And it was weird like just no stigma. And it's hard I think for Americans to really internalize that. And so it was one of the things where they were like, "Yo, we don't care if you're green or blue." Like, if you can do the work and you're good at what you do, we want you working here. No one cared that I was tattooed. No one cared that I didn't care. It was just so like in America, you hear all the time like merit-based. It was the first place I ever went to that like was just full accept.
Like they just didn't care. And so I know people say all these bad things and like there's definitely things I don't agree with or are different than American culture, but it opened up a new thing where I was literally running multi-billion dollar projects. From there, then co hit and that's when I was like, "Okay, man. Like they're going to be closed for like a year and a half, their borders."
And so I actually started LSE remotely in Saudi Arabia because they had the borders fully closed. So I didn't get out of Saudi Arabia. I had to get out through a repatriation flight through the US embassy where they fly you to DC and like you're on your own from here. And it was weird when I first enrolled, you know, I again I had never been through the process and so they had like my registration window was like Tuesday I could from like 9 to 10 your classes, but the Wi-Fi was like messed up in Saudi and I remember calling my friend.
I was like like crying because I had missed the window and I'm like, "Man, I let down everybody like I'm fucked." and and and she was like, "Why are you stressing, bro?" And I'm like, "Because now I can't go to school. Like, I missed the registration." And she assists him. She's like, "It's not a bus. Like, once it takes off, you can't get on." She's like, "Just email the school and like tell them what happens and they'll give you the classes."
And it was weird because there was certain things that I just didn't know. Like, you don't know. You don't know.
And for some reason, I thought like the window was gone.
Ken Rideout
Yeah.
Daniel Dart
And I remember it was like one of the hardest things of my life because like so many people were pulling for me and so excited. And I remember thinking like how am I going to going to tell them? And I got another thing which is these are kind of the reverberating effects that I'll kind of touch on. When I first started my fund um and I hate to put them on Frustrate. I was going to bank with Citizens Bank.
Ken Rideout
Yeah.
Daniel Dart
Right. You know, we set it up and we do all the thing and I look at my bank accounts and then we're going to set up the paperwork. People want to sign and it got caught up because someone on their team didn't want to bank someone who had been to prison.
Ken Rideout
Why wouldn't you want to put him on Front Street? I would want to put him. I'd be like, "You know what? Look at how [ __ ] shitty and stupid this is."
Daniel Dart
Yeah. So, but it was crazy. And at that time, I I didn't know because it got help up and risk. And I remember thinking, you know, this big article had come out on Yahoo and all these famous people had like backed me and I thought, man, is there some like law that I don't know about that? Like, I can't run a fund. So, I remember calling my friend Jeff Korzenik, who's the chief economist at Fifth Third Bank. Yeah.
And he's like, "Fuck, I don't know if there's a law. Like, let me call like the compliance." That chief compliance officer there's like, "No, there's no law. That's like a unilateral thing."
Ken Rideout
Hold on. One quick thing to your point about Saudi, that's what's effed up about in the US, like once you've been to prison, like you the the system is set up so much so that whether you agree with this or not, once you've been to prison, even if you paid your debt to society, they will make that system set up for you to fail.
Daniel Dart
Yeah. the stigma is is so crazy
And it's like
Yeah you can't do a lot of things and then even then like
And and and what I had said is I'm like how is it that like yo like I've done miraculous things right like the only guy at LSE one of the top schools in the history of man right then MIT which also I think has won best university for 20 years or something and I can't get banked like what does that for 20 million other Americans. And so, you know, eventually, you know, Stifel came in and banked me and, you know, citizens did call and apologize. But I remember thinking at that time the same way, like, man, I let down all these guys who were going to back my fund now.
I got to call them and be like, "Yo, I can't do it." And all of these different things that have happened. And so I think on the outside when we talk about like courage or failure or risk, there's all these little mini mountains that I have to climb along the way.
And even LSE when they let me in that the dean or whatever emailed me the next day and was like, "Please do good because like everybody's going to be watching,
You know, and so and I had a lot of things like that even I think at MIT like
Hold on. What were the two degrees you got at LSE?" Uh I got a theory in history of international relations and then um a social entrepreneurship and business finance.
Ken Rideout
Okay. And then how did you end up for so you get those two degrees graduate. How long did it take?
Daniel Dart
Two years.
Okay. And then how did you end up at MIT? So, initially I thought I wanted to do a PhD at LSE and I was just like more of like a quantitative like financey thing and I wanted to do it under this guy named Sir Julian Lrand who's like
You know he's a nighted economist like in in the ecom world like somebody you geek out on you know like you're just like this would be so [ __ ] cool I could just study and hang out with this [ __ ] guy for like five years
And he and and this other guy uh Jonathan Roberts who were like in the Marshall Institute they were both like Hey. Um, and they were both my professors during my time. They're like, "Yo, man, we would love you to do a PhD. Like, I think it would be fun working with you, but like you don't want to be a professor, you want to do a practitioner." And both of the the degrees you just did right now were like research, like, you know, kind of thesis driven degrees.
We think you would probably enjoy doing like an MBA.
Ken Rideout
Yeah.
Daniel Dart
So, then I was like, "Okay, well, I should research. Where should I do an MBA?" And then it really came down to MIT or Booth, you know, and I I chose MIT for a multitude of reasons. One of which was Goodwill Hunting, you know.
Ken Rideout
That's funny. That's why I grew up in Somerville, which is right next to Cambridge. But did you just when you say I came down to these two, like getting into those schools isn't easy.
Daniel Dart
It's really hard. Yeah. And so,
Ken Rideout
But I imagine you had a lot of good people at this point vouching for you cuz your cor your professional experience in all those like international uh roles is crazy.
Daniel Dart
Yeah. So now I had really strong kind of options and stuff like that and I also think the the public profile started to get up. So now I was like a known entity.
Ken Rideout
Y
Daniel Dart
And so yeah I talked to both of them and really it was like hey is there any like financial aid? What are the things I could get you know and then you know with my partner like where do I want to work from? Where do I want to be at? Like those type of things. MIT was the first to say like hey come here let's go and booth was like lagging like they were like
Yo like you know this is like your background's so unique and so and at that point I was still in London and so I was like okay if I'm going to make the move like I'm not trying to do last minute so I was then I wrote to a letter to Booth and I said hey you know um I'm going to accept the offer at MIT and and the dean at Booth we're actually still friends we've hung out a few times she wrote back like 20 minutes later was like no no no no no like call me like you know don't accept that and then there's a running joke now she goes well if you ever do a PhD you
Ken Rideout
know you boo the funny thing is with those schools when they want you and you have the need those schools their endowments are so big they don't have to charge anyone like they they can wave they can grant you the full free ride
Daniel Dart
Basically
But I also think
Ken Rideout
If you have need they'll pay for it
Daniel Dart
Once you once you I think get to a point where you add value to program in reciprocation, then it's super competitive. So like it's almost like a sports team like it's not like oh MIT gets everyone who wants to go like they have to compete for the talent against Booth or Stanford.
Um and so I went to MIT and and and that was great. How was that?
Ken Rideout
It was good.
Daniel Dart
While we were there, I I think you you know one of our mutual friends, Edgar Smith, I had to give him a shout out on this.
Ken Rideout
Edgar, for those folks just to give some background, Edgar was portfolio manager at USC, was an incredible ally to me when I was in a business development role, which when you're in business development role at a like fund or an asset manager, private equity venture, you call on endowments, pensions, foundations, and Edgar was in a role to essentially allocate to different managers.
I worked at a manager, so he had the ability to write like 2550 million at a clip. And you know if you manage $50 million you get paid two and 20 if it you know on the high end and you know you that's those are big big numbers. So those relationships are critically important and not that you know someone and you get an automatically get the thing but the point is when you have a relationship with guys like Edgar Smith or Pi Wang who's the CIO chief investment officer at Cedars-Sinai.
She was at Caltech and we had done some business together. These people have been so kind to me.
Like honestly like I'm getting choked up. They have been so kind to me cuz I was like a dope.
The only thing I offered any job I ever worked in was relationships and personality. No one was looking for me to like
Give them trade analysis, build them uh models. It was all relationships. And those Edgar and Paigy in particular along with several others were just so incredibly kind and generous with their time and they really like transformed my life not because they did business with me but because they welcomed me into this. I have a degree in sociology from Framingham State College. Wall Street wasn't waiting for me with open arms and I was working with people like yourself that had masters from MIT, masters from LSE, like one person with all these degrees.
So for me to be in good graces with these kind of decision makers was lifechanging, lifealtering even till now. Like when I see Pi, I'm like I love her.
Daniel Dart
Yeah.
Ken Rideout
And she's like and same with Edgar. I love him. He's like such a friend to me. And to your point, like they love you. I mean, they speak so glowingly of you, which is how we came to meet. But anyway, had to get that in.
Daniel Dart
Yeah. So, I'll I'll kind of put full circle in that. So, one of the things that is really important to me is reciprocation and specifically around criminal justice and prison re-entry and social mobility. And so when I was at MIT and even now I feel like there's a lot of interest sometimes in criminal justice reform today that didn't exist 20 years ago and and so I talked about at LSE at MIT like there was no criminal justice movement when I first got my felonies. Like it was just like yo like that [ __ ] doesn't exist.
And so when I was at MIT, I had talked about a few professors because I wanted to put together a program that taught financial literacy, entrepreneurship in jails and prisons. And so I really worked hard to put that together. And so it's still going on today. It's long-term program. They still teach in many jails and prisons in Massachusetts and beyond. But as I was putting that together, I ended up putting together a run as part of the speed project. Edgar joined the team and that's how
We met because I was like, "Hey, I want to do this
This run across the desert for 300 miles to raise money for this prison program.
Ken Rideout
It's from LA to Vegas and you race on a relay team of like six guys." So, people typically have like an RV, a bunch of jeeps, and they're following and one person's constantly running. The year you did it, I did it with a guy here in Austin called Nick Bare in the Bear Performance Nutrition, and it was, dude, it's hard. You're running every four, every couple hours for 36 hours, you know.
Daniel Dart
So,
Yeah. Yeah. Yeah. We followed right behind you. You guys beat us, man. You're fast. But yeah, it was wild. And I think
That was really important and probably the greatest greatest thing about MIT is it's a very entrepreneurial school. Once you're kind of in there, they kind of let you do whatever you want. And when I was there, I remember going like through all the processes talking to like the local sheriff and local correction thing and you know and even this one professor that I got an argument when I first met him like you know who ended up becoming my real big ally. I was like hey can you co-write this curriculum because I wanted to be like official MIT curriculum so I need you to write it.
Yeah. and ended up having a lot of fun. But that that's probably the best kind of memory I had for MIT and it's still going on today. And that's how I met met Edgar and and it was really cool. And now Edgar, you know, I consider him one of my my very very close friends, you know.
Ken Rideout
And so tell me how did you eventually start the Rock Yard
Rock Yard
Daniel Dart
Rock Yard Venture Fund. So, I knew that I wanted to launch a fund of my own probably as early as like 2017 when I first learned about I was like, "Hey, I want to be in venture." And it's weird because like in retrospect, it was clear I had to start my own fund, but so much of my life I've had to I've never gotten through the gatekeepers in a way where I could go through traditional systems. Yeah.
So, everything was like a first.
Yeah. And so I kind of knew already like I don't think I'm going to be able to get a great opportunity somewhere. If I want to do this, I'm going to have to do it on my own.
Ken Rideout
Yeah.
Daniel Dart
Right. And so
Ken Rideout
You didn't think you could get a job with those degrees working at a big venture fund?
Daniel Dart
I think the hard thing is like would I do I think that I would get it early on in a way where I'd be treated as an equal? Unfortunately, no. Because I think there's an an an aristocracy and I think a lot of times like identity is based on being special and I think a lot of people you know it's like how many people do we know who are billionaires that were born from billionaires and all these things and they have this like oh I'm God's gift but it's so important for them to believe that because anything else would be an assault on their identity.
Ken Rideout
Yes.
Daniel Dart
Right. It's like I always joke like climate was the best thing to happen to white people because it gave them a cause that like impacted them. Like there's no other adversity, but like climates our [ __ ] thing. And so,
You know, now as things have moved on, I have like so many great like supporters and advocates, people like Edgar and Py who are like, "Yo, we believe in you." But I think early on I just didn't have that. And that's why there's a there's a guy named John Arnold, a really famous, you know, former energy trainer
Ken Rideout
Who
Daniel Dart
Yeah. Yeah. Yeah. And then he started Centaurus and
And he's done a lot of um quotes for me and some articles, but like three, four years ago. And like I think there's very few people that would jump out early on and and do that headline risk.
Ken Rideout
Yeah.
Daniel Dart
You know, where they're like, "Yo, this guy deserves a chance." And so I knew I wanted to raise my own fund. And then there was um I would love to to say his name. He's a private guy and I can't say it, but there was one guy specifically that really put me into business that was like, "Yo, man, we believe in you. Start your own fund. We will anchor it. Like just go." And honestly, I was [ __ ] scared, man. And finally, he pulled me aside and was just like, "Don't be [ __ ] scared.
You're going to [ __ ] kill it." And And then one time he had this conversation and he was like, "Do you think I'm [ __ ] dumb?" And I remember being like, "What? What the [ __ ] are you talking about?" He goes, "Do you think you manipulated me?" And I'm like, "What?" He's like, "Because like I believe you'll be successful. The fact that you're scared means that you think I'm a [ __ ] idiot or something."
And that kind that kind of hit me and I was just like, he's like, "All of these people like you need to stop thinking you pulled a trick on all these people. like you need to
Ken Rideout
This guy is smart because that's exactly how I would be thinking subconsciously. It's like they don't they don't know how stupid I am. They know how stupid I think I am.
Daniel Dart
Yeah.
Ken Rideout
And then my wife would be like why do you think that? Like you keep doing it. It's like if I win a race I'm like
I got lucky man. Everyone here sucked. And they're always like how many races do you have to win before you're like everyone doesn't suck. Yeah.
And it dude I'm 50. I'll be 55 in two months. It's taken me a long time to realize like I'm good at some stuff.
Daniel Dart
But I know what you mean. That's the thing, like I'm good at some stuff and and then he sat me back. He's like, "At these other firms," cuz I had worked at some other firms now. And he's like, "You know how to do the job." And and there was a few people that that believed in me and they were like, "Yo, I I believe in you and like of course I want to help you succeed.
I don't want to help you succeed that much that I'm gonna invest this [ __ ] money in you. Like I'm investing that money in you because I think you're going to do well."
Yeah. And I think a lot of that it goes back to who you surround yourself with, you know? And I think um I'm just going to throw Edgar under the bus. I hope he don't don't get mad. But he's an investor of mine, right? So I'm just like I hope he don't listen to this and be like, "Yo, you put me off Frustrate." But I think
It was so interesting when he was like, "Yo, because I have so much respect for him."
Yeah. when he was like, "Yo, man, like I want to be part of this." And and people like that, then it's like you start to believe it. And then over time, you start to see more proof points.
Ken Rideout
Yep.
Daniel Dart
And like now, to be honest, like, and I'm not trying to be arrogant, but now I'm like, "Yo, I'mma [ __ ] crush this shit." Like sometimes I do [ __ ] and I'm like, "Yo, these [ __ ] like, you know, it's like and and I think I go back to earlier when we're talking about like tough guys on Twitter and I'm like, you know, I think about some of these, you know, these these big kind of famous businessman talk and I'm like, you're like, I know you're not tough because I've seen what tough looks like."
Ken Rideout
Yeah.
Daniel Dart
Right. Like that's not how tough moves. That's not how tough talks. And I think now as I'm doing it and leaning in and more and more and like got my sea legs under me, I'm like, "Oh shit." Like like not only am I going to do good, but I'm going to do [ __ ] great.
Ken Rideout
So tell me about the fun. You're on fund one.
Daniel Dart
So I'm on fund one. Uh
Ken Rideout
Can you say how big it is?
Daniel Dart
Uh well $5 million. Yeah. You know, but overall we manage a little over $15 million now cuz we've done a bunch of followons and breakouts. Um, fund two will be significantly bigger.
Ken Rideout
Definitely.
Daniel Dart
I'll turn it. So, it's interesting. I wasn't gonna go out and raise it until mid next year. Yeah.
But then
Probably about 3 weeks ago, I'm in San Francisco with someone and they're like, "Yo, I want to invest."
Ken Rideout
I was there with you, you nut.
Daniel Dart
Yeah. So, it was earlier that morning. I don't know if I told you the name, but it's it's a it's a big name. It's a big hedge fun guy. And he was like, "Yo, I want to invest. Like, send me the dice." I'm like, "Yo, the fund's closed." He's like, "For fund, too." And I'm like, "That's not till next year." He's like, "Well, send me the docs now. Like, I want my allocation. Like, just call it next year."
And I remember being like, "Oh, shit." And he's like,
He's like, "Bro, like pretty soon there's going to be no allocation." And then I'm excited. So, I tell this other guy who's probably been fun, too. And he's like, "Holy [ __ ] Well, I need to get my five bucks in. So, like, send them to me, too." And I'm like, "Oh, shit." And then um but but there was something I almost wish I could pull out my phone. So I ended up just doing this deal recently and um I was the first check in and even though I'm a small check I'm like yo man I want to invest in second time founder and uh wellknown guy and and he's like oh most small funds don't commit until there's a lead.
I'm like I don't give a [ __ ] Someday I'm going to be lead.
Ken Rideout
Is there anything more frustrating? So, I work as a placement agent for the people that don't know. Meaning, I raise money for private companies and help funds like yours and in big funds connect with investors like Edgar, PG, like I would make the intro and as a placement agent, I'm like registered rep affiliated with the broker dealer, all that stuff. So, you get paid a percentage of the money that you raised the like in theory.
And um nothing pisses me off more than when someone's like, "Dude, I love this deal, but I don't want to be the lead." I'm like, I I'm always like, "Are you a pussy?" Like what are you talking about? If you love the deal, like the the the company's going to pay for your attorney fees to like do the leave docks and negotiate everything. It it would drive me crazy when people like I'll be in, but I don't want to be the lead. Like I'm like what what?
Daniel Dart
So I end up doing a deal, right?
Ken Rideout
Yeah.
Daniel Dart
And and we have a small check comparatively. And so I check in with this morning. Hey man, just want to check in. How's the raise going? Like you know, I made a bunch of intros and he's like, bro, it's going great. I've talked to three. We're on like our third call. And he's like, "But the best thing is he's like, "Everybody that I've met who you've introduced has been super excited to meet me because they hold you in such high esteem." And these are like big tier one like famous firms, right?
And what I always say to people like, "Yo, I'm a lead investor. Like I have a small fund, but like if I had a $50 million fund, we wouldn't even go out to these [ __ ] guys. I'd do the whole [ __ ] myself."
Ken Rideout
Yeah. That's what I like.
Daniel Dart
And so like if I got conviction, I got conviction.
Yep. Right. And um you know I always joke like with Sequoia because I'm coming for you, you know, and it's like and I think that to me is like the the kind of fearlessness like of course does it mean they're better than me today? Yes. But like they weren't always the biggest and baddest and best.
Ken Rideout
I would say I would say to the contrary, does it mean that they're better than you? No. They're just bigger and I mean and they're different. Doesn't mean that they're better. I mean, there's plenty of big venture funds that suck and they're like I would tell founders like, "Yo, if you want to go in business with them, like, count all your fingers and toes cuz you ain't going to have them all when you're done." Yeah.
Daniel Dart
I think a lot of it is like you just need people that are going to fight for you.
Yeah.
Like in anything like it's like that saying like find your believers. Don't try to convince the skeptics. Yeah.
Even though it's hard to remember, you know, but I think it's like it's the same thing. It's like, hey man, like you know me being the first to commit, like the idea like if you don't raise the round or something and you fail, then [ __ ] that's the risk I take.
Ken Rideout
Yeah.
Daniel Dart
You know what I mean? But like this is the risk on business. Like this isn't downside minimization. This is upside maximization.
Ken Rideout
Exactly. You're a venture fund taking making venture bets. But I was I tell this story all the time. I was just telling someone this morning like you run into founders and you've get the the missionary or the mercenary, right? Like you get the mercenary and you're like and not one's not necessarily better than the other. You're like, I'm going to build this and then I'm going to sell it to this guy and they're going to buy it because once I have this many subscribers, they buy subscribers at this rate.
And then you run into a guy like Bill Shufelt who I love from Athletic Brewing and he's showing me around his brewery and I'm like, "Bill, this is wild. This is so great. Who do you think is going to buy this?" Like Anheuser-Busch. He looked at me like I was crazy and he's like, "I'm never selling this. I'm riding. I'm going to build this and run it forever." I'm like, "Oh, this is like a hardcore missionary."
Daniel Dart
Yeah.
Ken Rideout
And those are the kind of guys like they're both they both have value, but there's something about a missionary where you're like, I love the guy's passion like you know that he'll die to win.
Yeah. And that is to me from an investment from from an investor standpoint because I make a lot of small venture type best myself just I mean small checks but
I want to ride with the guy who's like no no we're going to die together.
Well what happens if this thing well I'll have to sell my house
Daniel Dart
You know he's like you know the guy's crazy. I I was talking to Bill Gurley. He came and spoke at our our summit a few weeks ago and and the Saturday before we hung out had a long conversation and he was like oh man you're going to do really good. And I was like, "Oh, why?" And he goes, "Because uh one, you're a fast learner and you're having a lot of fun."
Ken Rideout
Yeah.
Daniel Dart
And he's like, "That's really really hard to compete with." Yeah.
Over a long period of time.
Ken Rideout
Yeah.
Daniel Dart
Because other people if they're not having fun, they just run to gas. Y
And he's like that ability to learn fast with like the fun once it starts compounding and I think what he said then you have different problems to worry about like your multiple houses and your cars and like
Ken Rideout
House managers
Daniel Dart
You know but
Ken Rideout
What's the strategy of the fund
Daniel Dart
So we focus broadly on critical and foundational industries like what that really looks like is broadly industrial adjacent sectors
As well as a touch of healthcare
And the healthcare is because it's highly regulated so I really like that. And and the way I kind of explain it sometimes is I want like slow revenue businesses.
Ken Rideout
Yep.
Daniel Dart
Because like I think the switching cost is higher. Sometimes when you see stuff and it goes like one to 100 million, I'm always worried like damn if they could switch to you that fast like how fast can they switch away?
Ken Rideout
That's right.
Daniel Dart
And I think we're going to see a lot of that over the next few years. like companies that were massive like
Um and so to me I'm like yo I want really sticky critical [ __ ] that matters that's very hard to rip and replace which means it's also very hard to onboard.
Ken Rideout
Yeah,
Daniel Dart
You know and that's what I'm like looking for.
Ken Rideout
I got you. Well, if anyone listens to this wants to get in touch with Daniel, you can reach out to Daniel D. You can get in touch with me. I love it. I like I want to be involved too. I'm like I like the I like the energy. I like the tattoos. I like the crazy renegade spirit.
It's just appealing to me because like I view myself probably the same way you'd think of yourself as like an outsider. Even if people in the industry don't think of it, I feel like an outsider when I'm at those events. I feel like I'm the dumbest person there. Um I feel like I've slipped through the cracks. But I also feel like, oh, the minute that you doubt me, I'm going to like when I worked when I met Edgar, I was working at an asset manager at like $2 billion.
When I left, he had 5 billion in AI, but he had no business development. I would convince him to hire me and he was like this guy Jack McDow who ran a place called the Palisades Group who I love. He changed my life. I said to him at one point we were riding bikes together and I that's how I knew him and I said um oh Jack hire me hire me. He's like you don't know anything about business development. I was in I was on a trading desk for my whole career as a salesman and trader and uh I said after finally trying so many times I said I'll work for free for three months.
I had four kids. I was living in a house rent was $12,000 which I could barely afford. I was running out of money. I was working at a fintech startup that I helped a guy from Goldman start that I wasn't really making money. I knew it was a long shot. Long story short, he's like, "Yeah, okay." And I went there. After a few weeks, he's like, "All right, it's working. Here's like a normal finance salary that would allow me to pay my bills."
And dude, we went from 2 billion in two years to 5 billion. And we went to raise a discretionary fund, like a private equity internal fund. And we went to like Park Hill and all these big funds. And they like placement agent funds that help us raise capital. And they like laughed us out of there. And at one point in one of those meetings, the guy said, "Why do you think you can raise this money? You guys have no experience with discretionary capital." And it was it was a really unique situation that I knew couldn't lose.
Like we had this huge infrastructure, managing giant pools of residential mortgages and we were doing smaller trades and all the fallout assets we were marking like down 50% and selling them to like hedge funds and they were killing it. And I was like, if we had a fund, we could beat those match or beat those bids and close every trade like on the line versus 90-day closing and more downside pricing, repricing risk. They said, "Why do you think you can raise this money?" I said, "Dude, I think I'm going to win the [ __ ] Boston Marathon until someone beats me."
And dude, we raised 35 million in um trying to think if Peggy was in it. Caltech.
I hope I'm not violating their trust. And um we charged zero management fee because we had all the big infrastructure. We were managing money for like Soros, Apollo, like third point, the best of the best as separately managed accounts. We doubled the money in 26 months and we had no management fee but a 30% incentive and we made like $10 million on the first fund and then raised $150 million fund and bigger. And after two years, the guy said, Jack McDall comes to me and says, um, you're wasting your time.
You should be doing this on your own like you. And I was like, I've never worked for myself. what about health insurance? What like all these irrational risks and he was like, I'm going to give you 50 grand a month for the next year and you go start your own thing. If it doesn't work, come back, you work here. And I went and I met this David Sinclair, uh, the longevity professor from Harvard, um, geneticist. He wrote the book Lifespan. And we raised a bunch of money for his company, Life Bioscience in Boston.
And then I met all these like health and wellness guys. I met Andrew Huberman and my career went in a totally different direction. And but to your point, it was all about taking risks and believing in myself. I have four kids. I wasn't like in a place to be like, "Yeah, I'm going to go work for myself and leave this killer job."
Daniel Dart
But that's how I ended up in in Austin really is. So
I was thinking like, what should I do? And I was living in Boston and I end up going out to like this Irish pub with with John, right? So we're sitting there and he's like, "Okay, let me ask you this. if I could get you like a partner role at like Sequoia or Benchmark. And I kind of always said I'm like, is that what it's like to be a billionaire? And he was like, man, I'm being serious, right? And I'm like, [ __ ] And he's like, no, hypothetically, would you rather do that or would you rather do your own thing?
And I'm like, honestly, I think I'd rather do my own thing. And he's like, that's what I thought you'd say. Now that being said, what size fund increases your probabilistic for upside success early on? I'm like, well, a small fund. And it's like,
Okay, well then what do you need for a small fund? I'm like, okay, I need to reduce my living expense. I need to reduce this. I need to reduce that. And so then I was like, well, I could live in Austin. And he was like, you know, he's from Houston. He's like, dude, I think you'd love Texas.
Ken Rideout
Yeah.
Daniel Dart
And so I end up going home. And then I'm talking to Annie. I go, okay, we got to move to Austin. We're going to do this. And like even at 5 million, I can make it work. And I think it was the same thing. Like the minute I make a decision, it's like, bro, you're going to have to kill me to beat me.
Ken Rideout
Y
Right. Like, and it's like, it doesn't mean that I I think like, oh, I got it all figured out, but I know like push comes to shove. Like, there's no way I'm not going to give it 150 million%. Well, the reason that I know it's going to work is because the people that we've been talking about here today don't believe in you and aren't friends with you if they didn't think you would succeed. And people, friends, like the people that we've mentioned, don't let their friends fail without going down with the ship themselves.
And there's something to be said about relationships and the camaraderie. And it's almost like the Wall Street or finance version of prison gangs. It's like once you're in that crew, they look out for each other.
It's the same way. Once you run a foul of the crew, you're dead. You're out of the business.
Daniel Dart
100%. And I think even back about the deal I explained earlier was the first check, like the person who it came through was like a super famous Silicon Valley. He's like, "Hey, this is an interesting one. I think I might do it." Like an angel check cuz he's a very famous angel, probably the most famous angel. So I meet him and and the guy had invested in his first company. And so I'm like, "I'll do it." And then when I go to share it around, they're like, "Wow, this is great." Like, "Where did you find this?" And I'm like, "Oh, so and so shared it." and they're like, "Holy [ __ ] that's crazy."
And and it's the same thing. And the way I got to meet that person is they had done a deal in my space. Okay? So, I probably cold emailed them to try to meet me like five or six times and they never responded. Then, you know, about a year after trying to cold email, I see they do a deal in like supply chain. I was like, "Man, I wish you had told me." I'm like, "Bro, I've cold emailed you eight times. Don't you see how gritty I am?
Wouldn't you love to have me working on a portfolio company like that?" They wrote back like laughing and they're like,
"Okay, you have a really good point." I'm like, "Let's meet." And then they're like, "All right, let's get some time on the counter." And now we talk all the time, but I was just like, "Bro, like you've seen over the last year how much times I've hunted you down. Like, think what I would do for the people that I I'm working with." And you know, I've said that like, you know, I'm one of the big early investors in in Chad Rigetti, who founded Rigetti Computing, and now he's the new company Signal Dree, which is like really one of my breakout marquee investments.
And I had joked with him when I first was trying to get allocation. I'm like, "Bro, I am your Ray Donovan. I am your John. My
Ken Rideout
Favorite character."
Daniel Dart
Yeah. And so he was like, he was like laughing. But he's like, "Man, I think that's the greatest VC pitch ever."
Ken Rideout
That's awesome.
Daniel Dart
You know, I'm like, "Point me in a direction." And I think like you had said like you find the right people. At um MIT, one of my classmates was Howard Buffett Jr. He was uh uh Warren Buffett's grandson.
Yep. And he was like giving a talk one time to me and he's like, you know, my grandpa always says like if you surround yourself with great people, you will inevitably rise to meet their expectations.
Ken Rideout
Yes.
Daniel Dart
And so I kind of have that same thing where like again I want to do everything I can to put myself with the best people. And so like you know like that famous angel and the famous investor and he has a big fund too. I'm like yo man like that guy is winning. I need to work with that guy. And the thing about it is like I don't got to work on like two month timelines. It may take me five years,
But what I do know is once I'm your friend, I'm like extremely loyal. I'm extremely reliable. I'm extremely consistent. And so I think enough dots over a period of time, you see the trajectory, I can make it happen. And and that's where we're at. One thing that that also I want to say is I'm in the process right now of applying for a governor's pardon for California. So hopefully I get that, too.
Ken Rideout
Oh, let's go. Gavin Newsom, do something right today. Come on.
Daniel Dart
We'll see. So hopefully over the next year or two, you know, we could we could do a report back and let you know how that goes, man.
Ken Rideout
Well, listen, brother. It's so good getting to know you. It was great talking to you today. I hope people really enjoy this. And for the investor community out there, if you're a venture investor, like, let's talk. I like want to be involved. I want to help you. I love this.
Thanks for doing this, man. One quick thing, PSA, my book comes out March 10th. If you would be so kind as to pre-order available everywhere you buy books. Everything you want is on the other side of hard. Dan, you know that that's the truth.
Daniel Dart
They're about to send them out, too, cuz I got one when you told me about it in October or something and I just got an email today that said about to ship.
Ken Rideout
Well, you're on the VIP list, too, cuz I'm sending you some signed ones as well.
Daniel Dart
Amazing. I love that.
Ken Rideout
So, thanks for being with us, everyone. Daniel Dart, Rock Yard Ventures. Boom.
Daniel Dart
Thank you.
Ken Rideout
All right, guys. I hope you enjoyed that conversation as much as I did. Please take a quick minute to subscribe to the podcast wherever you're listening. This is a new show, so subscribing makes a huge difference. Please also take a minute to give it a review and leave a comment on Apple Podcast and on Spotify. You can also subscribe and leave a comment on YouTube. Again, this is really important for us, especially now since we're just getting started.
They make the show possible and honestly I love and use every single product we talk about on the show. You can learn more about me, this podcast and also find links to purchase my upcoming memoir at the other sideofhart.com. My new book is called everything you want is on the other side of hard and it comes out March 10th available everywhere you buy books or again go into the otherofhart.com. There's multiple links there where you can find all the retailers carrying the book. Thanks a lot for being with us and we'll see you next
Key takeaways
- Choose friends and mentors whose habits and goals are the ones you want to grow toward.
- A prison sentence can end while stigma continues to limit housing, work, and access to financial services.
- Dart says people who take a chance on you can help turn ability into a real opportunity.
- An early investment can mean accepting uncertainty because you believe in the founder and the work.
- Dart looks for essential businesses with high switching costs that are difficult to replace.
Nowhere to Hide
A weekly letter from Ken Rideout about doing the uncomfortable part, and the reasons we use to avoid it.
It starts with 3 Days, 3 Hard Things: one short story from Ken and one hard thing to do, every day for three days. Then one letter a week.
One letter a week. Unsubscribe any time. We never share your email.
