Coolest Person I Know Podcast

Ep. 3: Cameron Siasi, VP of Operations at the Label That Signed James Blake

Sajag Agarwal, Jake Geddas — Thu, 13 Aug 2026 11:00:00 -0400

Cameron Siasi is 27 and the founder of Clearnote, the contract platform for music and entertainment. He is also VP of Operations at Good Boy Records, the Los Angeles label that signed James Blake.

He started managing artists at 17 out of his hometown in Maryland. He found one artist at roughly 1,500 followers and watched her pass hundreds of thousands in three to four months. A producer he has managed since they were teenagers, Rayman on the Beat, has a credit on a 2x platinum Benson Boone album. Today he is also the founder of Clearnote, the contract platform he built for an industry where, in his words, the majority of music is not paid for whatsoever. Along the way he explains why the whole business is, as he puts it, an accounting error for the tech industry, argues that ignorance when you are young is the biggest superpower you can have, and tells the story of calling his shot on his now wife the first night he really met her, at 16.

It is one of the coolest jobs most people have never thought of as a job, told by someone who is very deliberate about who he bets on. Which is the whole reason this show exists, and the only question it ever really ends on: who's the coolest person you know?

🎧 Full episode: https://youtu.be/F0FkzC8hbxU
Subscribe: http://www.youtube.com/@coolestpersoniknowpod

Production note: streaming payouts vary a lot by market, plan type and distributor, exactly as Cameron says on tape. As a rough public benchmark, a million streams tends to land closer to $3,000 to $5,000 than to any single fixed number.

(00:00) - The coolest job most people don’t think is real
(00:37) - Meet Cameron Siasi, and where the name comes from
(01:52) - Managing artists at 17: the Maryland origin story
(06:27) - Inside the black box: what a record label actually does
(10:53) - The middle class of music, and securitizing artists
(15:27) - Why being young and a little deluded is a superpower
(20:41) - Falling in and out of love with New York
(21:39) - Third spaces, and how to actually meet people
(25:11) - A perfect NYC weekend: venues and where to eat
(27:47) - How he scouts talent, and where the money really goes
(33:39) - Calling his shot: the story of his wife
(35:33) - The near miss, the 30 items, and a platinum record
(39:06) - Signing James Blake, the label’s ethos, and building Clearnote
(46:30) - The underbelly: what it costs to found a company
(50:11) - The sauna, and the Eric André story
(51:45) - An accounting error for the tech industry
(53:46) - Who’s the coolest person you know?

Ep. 2: Undrafted, Hamstring Torn Off the Bone, and He Still Made 4 NFL Teams | Jake Bargas

Sajag Agarwal, Jake Geddas — Mon, 27 Jul 2026 09:00:00 -0400

Undrafted out of UNC, Jake Bargas made the NFL the hard way. He signed with the Minnesota Vikings as an undrafted free agent in 2020, and his very first NFL game was on Christmas Day in the Superdome. From there he became a true journeyman: four teams, a 72-hour cameo with the Chicago Bears, and weeks grinding on the practice squad.

The road there was brutal. A week before his senior season at UNC, Bargas tore his hamstring off the bone and the agent calls went silent. That's where his "24-hour rule" was born: give yourself one day to feel sorry for yourself, then get back to work. To claw his way back after a cut, he cold-called GMs and even DM'd coaches (Falcons coach Arthur Smith, a fellow Tar Heel, actually answered) with a pitch built on pure humility: "I'll fill up the waters, man. I just want another chance." He breaks down the roster math most fans never see (90 in camp, cut to 80, then 70, and only 53 make the active roster, where "you have to take food off someone else's plate"), and why he calls going undrafted "the greatest gift" for keeping him humble. The kicker: even with NFL money, he still drives the same car he had in high school.

Then came New York, "the most competitive place in the world." Bargas traded the league for commercial real estate at JLL, where a tired "yes" to Messi tickets at a networking event turned into a closed deal six months later. Now he's betting on the New York to South Florida migration, brokering tenants into West Palm, Miami, and Tampa. Sajag and Jake Geddes get into all of it from NYC's Living Room in Midtown Manhattan, right up to the one question every guest has to answer: who's the coolest person you know?

🎧 Full episode: https://youtu.be/qQy7FaVa0ro
Subscribe: http://www.youtube.com/@coolestpersoniknowpod

(00:00) - Cold open: “I’d give up everything to go back”
(00:32) - Intro & credentials: NFL to commercial real estate
(01:13) - Boca roots: “My first word was ball”
(06:02) - The NFL journey: undrafted, the hamstring, the grind
(20:45) - The body as an investment
(22:10) - The locker room: the safest place in the facility
(23:08) - Journalism, media & the NFL “education”
(28:08) - College nostalgia & the NIL money era
(30:46) - The pivot: NFL to real estate at JLL
(34:06) - NYC’s Living Room: the city that never stops
(38:37) - Life philosophy & giving back
(40:30) - Personal: the long game
(42:55) - The Florida play: riding the migration
(44:25) - Who’s the coolest person you know?

Ep. 1: Rory Garton-Smith, the Sony-Signed Producer Whose App Passed Instagram to #1

Sajag Agarwal, Jake Geddas — Mon, 27 Jul 2026 09:00:00 -0400

When Checkmate passed Instagram to hit #1 on the App Store (above ChatGPT, on $0 in ad spend, built by a team of five), co-founder and CTO Rory Garton-Smith was on vacation in Fiji. His honest reaction: "I felt sick."

Here's the part that doesn't compute. Before tech, Rory Garton-Smith was a Sony-signed producer and DJ under the name Elk Road. He put a Britney Spears remix of "Toxic" on SoundCloud that went viral overnight, and Britney Spears' management messaged him just to say "We like this." He once had to follow the Jack U set from Skrillex and Diplo, told not to touch the CDJ for a six-minute outro he still calls "the longest six minutes of his life." He also traded oil futures off the shadows in satellite images of oil tanks, taught himself to code, and cold-DM'd his way into a job at Apple.

Now Paris Hilton is personally on his cap table and The Chainsmokers help him recruit engineers away from Meta. We also get the real NYC texture: Rao's ("you need to know a crime family"), Cafe Cluny, the Erewhon status tax, and Noriel's Shabbat, before Rory Garton-Smith answers the one question we ask everyone: who's the coolest person you know?

🎧 Full episode: https://youtu.be/z-QrfW28wiQ
Subscribe: http://www.youtube.com/@coolestpersoniknowpod

(00:00) - Cold open
(05:36) - Intro: the Sony-signed producer who became a founder
(06:28) - Perth, camels & growing up in Australia
(20:16) - Trading oil futures off satellite photos
(21:30) - Teaching himself to code into Apple
(25:50) - Britney Spears & the SoundCloud years (Elk Road)
(34:32) - Following Skrillex & Diplo: the longest six minutes
(38:16) - NYC’s Living Room: Rao’s, Cafe Cluny, Erewhon
(45:53) - Advice: networking is not networking
(52:24) - Checkmate passes Instagram to #1 on the App Store
(57:41) - Paris Hilton & The Chainsmokers on the cap table
(01:04:06) - Who’s the coolest person you know?