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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.

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“once I'm your friend, I'm like extremely loyal. I'm extremely reliable. I'm extremely consistent.”
Daniel Dart

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.

Read the transcript

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,

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.

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