LIVE @ YC Demo Day | Nate Bosshard, Joshua Reeves, Joshua Browder, Burkay Gur, Theo Browne & MORE

**Jordi Hays** (0:00)
You're watching TBPN.

**John Coogan** (0:03)
Today is Tuesday, September 9th, 2025 We are live from the Palace of Party Rounds. We are at YC Demo Day. The batch is fall 2025, right? F 2025, because it used to just be winter and summer, but now they've added, it's a quarterly batch. And so I believe we're in fall, is that right? Yeah. And so we are here with Nate. Introduce yourself, tell the stream who you are, why you're here.

**Nate Bosshard** (0:28)
Nate Bosshard, friend of the pod.

**John Coogan** (0:30)
The first time you came on was at the first time we did YC Demo Day, two quarters ago.

**Nate Bosshard** (0:34)
Been in the Bay Area for longer than I care to admit, 2008, I bounced around a few technology companies, spent some time at some institutional VC firms, have dabbled as an entrepreneur and now have a seed fund.

**John Coogan** (0:45)
Take it back further, how did you make your first dollar on the internet?

**Nate Bosshard** (0:49)
I sold used records on eBay.

**John Coogan** (0:52)
We used records. This is 2001

**SPEAKER_4** (0:55)
Vinyl guy.

**John Coogan** (0:56)
This is crazy because I sold record players on eBay. I sold DJ equipment.

**Nate Bosshard** (1:01)
As we know, as everything becomes more digital, tactile, physical things become more important.

**John Coogan** (1:06)
So I was an early adopter there. Was the ARB, so my ARB was international shipping. Basically, people wanted top tier DJ gear in Australia and they couldn't get it because the companies wouldn't export or was it more about going in, what do they call it, not crate digging. Crate digging, finding stuff that wasn't available in Ohio and then you ship it there or New York and LA.

**Nate Bosshard** (1:29)
Wisconsin, you would travel up and down the Mississippi River corridor, hitting up antique shops, getting career, soul, funk, jazz, psychedelic rock records and then you would sell them at a 10X markup to our friends in Japan.

**John Coogan** (1:40)
That's cool, that's cool. We have one more lightning round question.

**SPEAKER_4** (1:43)
Japan was your exit liquidity.

**John Coogan** (1:45)
We're starting with the lightning round. A most underrated or greatest entrepreneur of all time, who you got?

**Nate Bosshard** (1:51)
Oh, God.

**SPEAKER_4** (1:52)
Underrated or greatest is actually kind of hard to throw.

**John Coogan** (1:55)
Wait, wait, wait. What's the actual? So we're going to ask, we're going to try and ask every single person who comes on the stream how they made the first dollar on the internet and what their favorite entrepreneur is. Favorite. It could be anyone.

**Nate Bosshard** (2:09)
I'm going to go over the last decade, the last five years. I think Andrew Dudum from Hymns and Hers is a great, the fastest consumer company to go public.

**John Coogan** (2:18)
Yeah, that's true.

**Nate Bosshard** (2:19)
The only successful consumer smack trading at $11 billion.

**John Coogan** (2:23)
Yeah, they went out as a smack, but then they actually held the price.

**Nate Bosshard** (2:25)
He is an absolute killer.

**SPEAKER_4** (2:27)
And he's got a retail army.

**Nate Bosshard** (2:29)
Exactly.

**John Coogan** (2:29)
Which is weird.

**SPEAKER_4** (2:30)
Not every boardroom general can lead a retail army.

**Nate Bosshard** (2:34)
And I would just, I think Andrew is incredibly underrated. I'm not going to say all time, but in the last cold cycle.

**John Coogan** (2:40)
But we're going favorite. We're not going greatest.

**SPEAKER_4** (2:42)
There was some recent news that they didn't compounding, like generally get like a green light, which is very good for him.

**Nate Bosshard** (2:51)
Yeah, they've had a great kind of new wave with the...

**John Coogan** (2:55)
Yeah, like a regulatory royal flash has been kind of drawn. And there's been a lot of uncertainty about which way the chips would fall. And they got lucky.

**Nate Bosshard** (3:04)
And I want to give one other shout out to the founder, Hillary Coles, who also doesn't get a lot of publicity, but she is also an incredible founder and important to the success of the company.

**SPEAKER_4** (3:14)
Fantastic. Well, I have to put you in the true sound. This is Y Combinator Demo Day, Summer 2025

**John Coogan** (3:19)
Oh, this is summer.

**SPEAKER_4** (3:20)
This is summer.

**John Coogan** (3:21)
This is demo day.

**SPEAKER_4** (3:22)
We're starting fall.

**John Coogan** (3:23)
Fall batch. So we met some founders who had AF, who were, I think, going into the fall batch, but they've been accepted. They'll be joining the next batch. I believe so.

**SPEAKER_4** (3:31)
Yes.

**John Coogan** (3:31)
Oh, great. My first YC was summer.

**SPEAKER_4** (3:34)
S25.

**John Coogan** (3:34)