Ted
Josh
Intersection
Ted
NYC, finance & tech
Lower Manhattan, suits, the Seaport era
mid-80s
Josh
NYC, post-Duke
Same city, same suits, same bars (probably)
Ted
Building toward When.com
Web calendar, early consumer internet
1996
Josh
Co-founds RadioCo → Spinner.com
Internet music, July 1996
1999 — AOL acquires both
Ted · March 1999
When.com → AOL
$225M. Then VP, AOL Shopping & You've Got Pictures.
Josh · May 1999
Spinner.com → AOL
$320M. Then VP, AOL Music (Spinner, Winamp, Shoutcast).
Ted
AOL VP era
Shopping & Pictures, 1999–2000
1999–2000
Josh
AOL VP era
GM of AOL's music brands
Ted
Post-AOL: founder & builder
Multiple startups, indie projects
2000s
Josh
Co-founds Grouper → Crackle
Acquired by Sony, 2006, $65M
Ted
Building, advising, investing
Independent technologist
2010s
Josh
Co-founds Freestyle Capital
Early-stage VC, ~decade-long run
Ted
OpenClaw, AI agents
Building Gabriel, Raphael, and the runtime they live in
2020s
Josh
Co-founds Climactic
$65M climate-tech fund, Managing Partner
Ted
Walking around Lower Manhattan
Asking an AI about old bars
today
Josh
Walking around Lower Manhattan
…with Ted, comparing notes
Loading Josh's picks…
The 1986 NYC suit-and-suspenders pickup circuit
Harry's at Hanover Square · North Star Pub · Fluties · Harbour Lights · Suspenders
Dorrian's Red Hand · Jim McMullen's · TGI Fridays (1st & 63rd) · Ruelles
Ask Raphael for the full breakdown.
Harry's at Hanover Square · North Star Pub · Fluties · Harbour Lights · Suspenders
Dorrian's Red Hand · Jim McMullen's · TGI Fridays (1st & 63rd) · Ruelles
Ask Raphael for the full breakdown.
Ted — building OpenClaw, walking the Seaport.
Josh — Climactic, climate tech, also walking the Seaport.
Both still wear suits sometimes. Neither is trying to meet girls anymore.
Josh — Climactic, climate tech, also walking the Seaport.
Both still wear suits sometimes. Neither is trying to meet girls anymore.