Coolest Person I Know Podcast Transistor (https://transistor.fm) https://feeds.transistor.fm/coolestpersoniknowpod Coolest Person I Know is a New York City interview podcast hosted by Sajag and Jake. Each episode, they sit down with one genuinely fascinating person from their combined world — chefs, restaurateurs, club and nightlife operators, pro athletes, musicians, and the characters who give the city its energy — and go hunting for the one story nobody else gets them to tell. Part back-room-of-a-great-bar hang, part real curiosity, always the story behind the story. New full episodes every other week. © 2026 Sajag Agarwal, Jake Geddas 04838b1a-b721-58a7-8577-997bde7975ea yes Sajag Agarwal Jake Geddas en Tue, 28 Jul 2026 05:45:13 -0400 Tue, 28 Jul 2026 05:46:05 -0400 http://coolestpersoniknow.com https://img.transistorcdn.com/hGvmkrhoITAObttZrj19_-_1taKLtVNtLPQrLl1eVi4/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS84N2Nh/NjhlOGUxMWExZTFl/NDk0NTQwNDBjZGQz/NWNjNi5wbmc.jpg Coolest Person I Know Podcast http://coolestpersoniknow.com episodic Sajag Agarwal, Jake Geddas Coolest Person I Know is a New York City interview podcast hosted by Sajag and Jake. Each episode, they sit down with one genuinely fascinating person from their combined world — chefs, restaurateurs, club and nightlife operators, pro athletes, musicians, and the characters who give the city its energy — and go hunting for the one story nobody else gets them to tell. Part back-room-of-a-great-bar hang, part real curiosity, always the story behind the story. New full episodes every other week. Coolest Person I Know is a New York City interview podcast hosted by Sajag and Jake. @coolestpersoniknowpod sajag@coolestpersoniknow.com No No Ep. 1: Rory Garton-Smith, the Sony-Signed Producer Whose App Passed Instagram to #1 1 1 Ep. 1: Rory Garton-Smith, the Sony-Signed Producer Whose App Passed Instagram to #1 full 64a73517-23ca-4e38-b6f1-66bf6e1036bf https://coolestpersoniknow.com/episodes/ep-1-rory-garton-smith-the-sony-signed-producer-whose-app-passed-instagram-to-1 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?
]]> 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?
]]> Mon, 27 Jul 2026 09:00:00 -0400 Sajag Agarwal, Jake Geddas Sajag Agarwal, Jake Geddas 4040 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?
]]> Rory Garton-Smith, Checkmate, Coolest Person I Know, Elk Road, Britney Spears, Apple, Paris Hilton, The Chainsmokers, tech founder, startup, NYC podcast, music to tech Yes Sajag Agarwal Jake Geddas Rory Garton-Smith Ep. 2: Undrafted, Hamstring Torn Off the Bone, and He Still Made 4 NFL Teams | Jake Bargas 2 2 Ep. 2: Undrafted, Hamstring Torn Off the Bone, and He Still Made 4 NFL Teams | Jake Bargas full b151dedd-f45f-49c2-aac8-1e6fe6445f2c https://coolestpersoniknow.com/episodes/ep-2-undrafted-hamstring-torn-off-the-bone-and-he-still-made-4-nfl-teams-jake-bargas 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?
]]> 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?
]]> Mon, 27 Jul 2026 09:00:00 -0400 Sajag Agarwal, Jake Geddas Sajag Agarwal, Jake Geddas 2718 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?
]]> Yes Sajag Agarwal Jake Geddas Jake Bargas